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Please login to access the full content or check if you have access via Method 1: Addition of P—H Compounds to Aldehydes or Ketones in the Presence of Amines, or to Imines

DOI: 10.1055/sos-SD-030-00514

Yamashita, M.Science of Synthesis, (200730649.

An efficient and general method for preparing 1-aminoalkylphosphonates is the three-component reaction of aldehydes, amines, and dialkyl phosphonates. Addition of the PH group of phosphonates to ketones or aldehydes in the presence of amines is a simple, efficient, and general method to prepare 1-aminoalkylphosphonates, which have received increasing attention as they are key substrates in the synthesis of organophosphorus compounds such as phosphonopeptides, and also have been widely studied for their attractive biological activities as, for example, enzyme inhibitors, antibiotics and other pharmacological agents, herbicides, and haptens of catalytic antibodies.[‌4‌‌8‌]

Mee Meeeeee-eeee eeeeeeee eeee eeeee eeeee eeeeeee eeeeeee eeeeeeeeeeee, eeeeeeee eeeeeeeee, eee eeeeeee ee eeeeeeeee eeeeeeeeeee ee Meeeee 8.[‌8‌]

Meeeee 8 Meeeeee-Meee Meeeeeee eeeeeee Meeeeee Meeeeeeeeeee, Meeeeeee Meeeeeeee, eee Meeeeee[‌8‌]

Meeee eeeeeee-eeee eeeeeeeeee, eeeeee eeeeeee ee eeeeeee ee eeeeeeeee 8-eeeeeeeeeeeeeeeeeeeeee ee eeee eeeeee eeeee eeee eeeeeeee eeeeeeeeee, ee eeeeeeeeeee ee Meeeeee 8 eee 8. Meeeee-eeeeeee-eeeeeeeee eeeeeeee eeeeeee ee ee eeeeeeeee eeeeeee eee eeeeeeeee ee 8-eeeeeeeeeeeeeeeeeeeeee eeee eeeeeeee eee eeeeeee eeeeeeeeeeee eeeee eeee, eeeeeee-eeee eeeeeeee eeeeeeeeee.[‌88‌]

Meeeee 8 Meeeeee-Meee Meeeeeeee ee 8-Meeeeeeeeeeeeeeeeeeeee Meeee Meeeee Meeeeee eeeee Meeeeeeee Meeeeeeeeee[‌88‌]

Meeeeeeeeee 8

M8 M8 Meee (eee) Meeee (%) Mee
Me Me 8 88 [‌88‌]
8-Mee Me 8 88 [‌88‌]
8-eMeM8M8 Me 8 88 [‌88‌]
8-M8MM8M8 Me 8 88 [‌88‌]
Me Me 8 88 [‌88‌]
MM=MMMe Me 8 88 [‌88‌]
Me 8-M8MM8M8 8 88 [‌88‌]
8-Mee 8-M8MM8M8 8 88 [‌88‌]
8-eMeM8M8 8-M8MM8M8 8 88 [‌88‌]
Me Me 8 88 [‌88‌]
MM=MMMe Me 8 88 [‌88‌]
MM=MMMe MM8MM8MM 8 88 [‌88‌]
Me MM8MM8MM 8 88 [‌88‌]

Meeeee 8 Meeeeee-Meee Meeeeeeee ee 8-Meeeeeeeeeeeeeeeeeeeee Meeee Meeeee-Meeeeee-Meeeeeeee Meeeeeee Meeeeee[‌88‌]

Meeeeeeeeee 8

M8 Meee (e) Meeee (%) Mee
Me 8 88 [‌88‌]
(MM8)8Me 8 88 [‌88‌]
Me 8 88 [‌88‌]
Me 8 88 [‌88‌]
8-MeMM8M8 8 88 [‌88‌]
8-MeM8M8 8 88 [‌88‌]
8-MeM8M8 8 88 [‌88‌]
8-MeM8M8 8 88 [‌88‌]
8-MM8M8 8 88 [‌88‌]
8-Mee 8 88 [‌88‌]
MM=MMMe 8 88 [‌88‌]
eeeeeeee 8 88 [‌88‌]
8-eeeeeeee 8 88 [‌88‌]
8-eeeeeeee 8 88 [‌88‌]

Meeeeee-eeeeeeeee eeeeeeee eeeeeee ee eeeeeeeeeee eeee eeeeeeeee eeeeeeeeeee eeeee eeeeeee-eeee eeeeeeeeee eeeee 8-eeeeeeeeeeeeeeeeeeeeee ee eeee eeeeeeee eeeee eeee eeeeeeeee eee eeeeeee eeeeeeeeeee (Meeeee 8). Meee eeeeeeeee ee eeeeee eee eee eeeeeeee ee eeeee.[‌88‌]

Meeeee 8 Meeeeeeee-Meeeeeee Meeeeee-Meee Meeeeeeee ee 8-Meeeeeeeeeeeeeeeeeeeee Meeee Meeeee-Meeeeee-Meeeeeeee Meeeeeee Meeeeee[‌88‌]

Meeeeeee(M) eeeeeeee/eeeeee eee eee eeee eeeeeeee ee ee eeeeeeeee Meeee eeee eeeeeeee eee eee eeeee-eeeeeeeee eeeeeeee ee eeeeeeeee, eeeeeeee eeeeee, eee eeeeeee eeeeeeeeeee ee eeeeeee eeeeeee 8-eeeeeeeeeeeeeeeeeeeeee (Meeeee 8).[‌88‌]

Meeeee 8 Meeeeeee(M) Meeeeeee/Meeeee Mee Meeeeeeee Meeeeeee ee Meeeeeeee, Meeeeeee Meeeee, eee Meeeeee Meeeeeeeeee[‌88‌]

Meeeeee 8-[(eeee-eeeeeeeeeeeeee)eeeee]eeeeeeeeeeeeeeeee eee eeeeeeee ee e eeeeeee, eee-eee, eeeeeeeeeeee-eeee eeeeeeeee eeeeeeee eeee-eeeeeeeee, Meeeeee-eeee eeeeeeee ee eeeeee eeeeeee eeeeeeeee ee M-(eeee-eeeeeeeeeeeeee)eeeeee eeeeeeeee ee eeee ee eee eeeeee ee eeeeee eeeeeee ee 8-eeeeeeeeee 8-eeeee eeeeeeee 8.[‌88‌] Mee eeeeeeeee ee eeeeeee 8-[(eeee-eeeeeeeeeeeeee)eeeee]eeeeeeeeeeeeeeeee 8 eeeeeeee ee eeee eeeee eeee eeeeeeeee eeeeeee eeeeee. Mee eeeeeeee eeeeeeeeeee eeeeeeeeee ee eeeeeee eee eee eeeeeeeee ee eee M,M-eeeeeee eee eeeeeeee: (e) ee eeeeeeeeeee ee 8-eeeeeeeeeeeeeee eeee ee eeee M-(eeee-eeeeeeeeeeeeee)eeeee 8, eeeee ee eeee eeeeeee ee eeeeee eeeeeee eeeeeeeee ee eeee eee eeeeeee, ee (e) e eeeeee MM8 eeeeeeeee eeeeeeeeeeee eeeeeee eeeeeeee ee eee eeeeeee. Mee eeeeee eeeee eeeee ee Meeeee 8 eeeee ee ee eee eeee eeeeeeeee eeeee ee eeeeeeeeeee eee eeeeeeeeee eeeeeeeeeee.[‌88‌,‌88‌]

Meeeee 8 Meeeeeeee ee Meeeeee 8-[(eeee-Meeeeeeeeeeeee)eeeee]eeeeeeeeeeeeeeeee eee 8-Meeeeeeeee 8-Meeee Meeeeeee[‌88‌,‌88‌]

Meeeeeeeeee 8

M8 Meeee (%) ee 8 Meeee (%) ee 8 Mee
M 88 88 [‌88‌]
Me 88 88 [‌88‌]
Me 88 88 [‌88‌]
Me 88 88 [‌88‌]
eMe 88 88 [‌88‌]
Me 88 88 [‌88‌]
Me 88 88 [‌88‌]
8-MeMM8M8 88 88 [‌88‌]

8-Meeeeeeeeeeeeeeeeeeeee eee/ee eeeee eeeeeeeeeeee eeeee eee eeeeeee eeeeeeeeeee ee e eeeeeeee eeeeeeee eeeeeeee eeee eeeeeeeee, eeeeee eeeeeeeee, eee eeeeeeeee eeeeeeeee (Meeeee 8).[‌88‌]

Meeeee 8 8-Meeeeeeeeeeeeeeeeeeeee eeee Meeeeeeee, Meeeee Meeeeeeee, eee Meeeeeeee Meeeeeeee[‌88‌]

Meeee[8]eeeee eeeeeeeeeee ee eeeeeeeeee 8-eeeeeeeeeeeeeeeeeeeeee eee eeeeeeee ee eee MeeeeeeeeMeeeee eeeeeeee ee 8,8-eee(8-eeeeeeeeeee)eeeee[8]eeeeee eeee eeeeeee eeeeeeeeeee ee eeeeeeeee eeeeeee ee eeeee ee Meeeee 8; eee eeeeeeee eee ee eeeeeeee eee eee eeeeeeee eeeeeeeee ee eeeeeeeeeee eeeeeee.[‌88‌]

Meeeee 8 Meeeeeeee ee Meeee[8]eeeee Meeeeeeeeee ee Meeeeeeeee 8-Meeeeeeeeeeeeeeeeeeeee[‌88‌]

M-Meeeeeeee eeeeeee 8-eeeeeeeeeeeeeeeeeeeeee eee -eeeeeeeeeeeeeeeeee eee eeeeeeeeeee ee eee eeeee eeeeeeee ee eeeeee eeeeeeeee, eeeeeeeee, eee eeeeeee eeeeeeeeeeeeeeeeee, ee eeeee eeeeeeeeeeeeeeeeeeeeeeee (Meeeee 8).[‌88‌]

Meeeee 8 Meeeeeee ee Meeeee Meeeeeeee, Meeeeeeee, eee Meeeeee Meeeeeeeeeeeeeeeee ee Meeee Meeeeeeeeeeeeeeeeeeeeeee[‌88‌]

8-Meeeeeeeeeeeeeeeeeeeee eee ee eeeeeeee ee eee eeeeeee eeeeeeeeeee eeeeeeeee eeeee-eeeeeeeee eeeeeeee. Mee eeeeeeee ee e eeeeee eee eeeeeee eeeeee eee eee eeeeeeeee ee 8-eeeeeeeeeeeeeeeeeeeeee ee eeee ee eeeeeeeee eeeeeeee eeeeee eeeee eeeeeee-eeee eeeeeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeee 8-Meeeeeeeeeeeeeeeeeeeee ee Meeeeee Meeeeeeeeee Meeeeeeee Meeee-Meeeeeeee Meeeeeee[‌88‌]

Meeeeee eeeeeeeeeee/eeeeeee eeeee eeeeeeeee eeeeeeeee ee 8-eeeeeeeeeeeeeeeeeeeeee eeee eeeeeeeee ee e eeeeee eee eeeeeee eee-eee eeeeee (Meeeee 88).[‌88‌] Mee eeeeeeee eeeee eeeeeeeeeeeeeee 8-eeeeeeeeeeeeeeeeeeeeee eeee eeeeeeeee eeeeee eeeeee eeeeee eeee ee 8-eeeeeeeeeeeeeeee eee 8-eeeeeeeeeeeeee eee eeee ee eee ee eee eeeee eeeeeeee eeeeeeeeee (Meeeee 88). (M)-(+)-8-Meeeeeeeeeeeeeee eeeeeee eeeeeeeeeeeee (M)-8-eeeeeeeeeeeeeeeeeeeeee eee (M)-()-8-eeeeeeeeeeeeee eeeee eeeeeeeeeeeee (M)-8-eeeeeeeeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeee eeeeeeeeeee/eeeeeee eeeee. Mee eeeeeee eeeeeeeeeeeeeee ee eeeeeeeeeeee ee eeee-eeeeeeee-eeee eeeeee.[‌88‌]

Meeeee 88 Meeeeee Meeeeeeeeee/Meeeeee Meeee Meeeeeeee Meeeeeeee ee 8-Meeeeeeeeeeeeeeeeeeeee eeee Meeeeeeee[‌88‌]

Meeeee 88 Meeeeee Meeeeeeeeee/Meeeeee Meeee Meeeeeeee Meeeeeeee ee Meeeeeeeeeeeeee 8-Meeeeeeeeeeeeeeeeeeeee eeee Meeeeeeee[‌88‌]

Meeeeeeee eeeeeeeeee eeeeeeeee ee 8-eeeeeeeeeeeeeeeeeeeeee eee eeeee eeeeeeee eeeee eeeeeeeeeeeeeeeeeee8,8-ee-8-eeeeeeee (MeMM) eeeeeeeee ee eeeeeeeeee eeeeeeeee. Meeee eeeeeeeeeeeeeeee eeeeeeeee eeee eeeeeeeee eeeeee 8-eeeeeeeeeeeeeeeeeeeeee ee eeeeee ee eeee eeeeeeeeeeee eeeeee. Mee eeeeeeeee eeeeeee (MMM) eeeee e eeeeee eeeeeeeeeeee eeeeee eeee eeeeeeeee ee eeeeeeeeee (MeMM) ee eeeeeeeeeeee (MeMM). Meeeeeeeeeee eee eeeeeeeee eee eeeeee ee eeeeeee eeeee e eeeeeeee (MMM ee MMM, eeeeeeeeeeee) ee eeeee eeeeeeeeeeeeeeeeee (Meeeee 88). M eeeeeeee eeeeeeeee eeeee eee eee eeeeeeeeee eeeeeeeeeeeeeeeeeeee ee eeeeee eeeeeeee eeeeeeeeeeeee ee eeeeeeee eeeeeeeeeee eee eeee eeeeeeeeeeee ee eee eeeeeeeee eeeee ee eee eeeeeeeeee ee eee eeeeeeee. Mee eeeeeeeeeee eeeeeeee eeeeeeeee eeeee eeeeeeeee eeeeeeeeee eeeeeeee ee eee eeeee, eeeee, eeeee eeeeee eeeeeeee eee eeeeeeeeeeeeee, eeeee eee 8-eeeeeeeeeeeeeeeeeeeee eee eeeeeeeeeee eee eeeeeeee.[‌88‌]

Meeeee 88 Meeeeeeee Meeeeeeeee Meeeeeeee ee 8-Meeeeeeeeeeeeeeeeeeeee Meeee MeeeeeeeeeMeeeee Meeee8,8-Me-8-eeeeeeee Meeeeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 Meeeee Meeeeeeee (eee%) Meee (e) ee (%) Meeee (%) Mee
eMe (8-MeMM8M8)8MM MMM (88) 88 88 88 [‌88‌]
eMe (8-MeMM8M8)8MM MMM (88) 88 88 88 [‌88‌]
eMe (8-MeMM8M8)8MM MMM (88) 88 88 88 [‌88‌]
eMe (8-MeMM8M8)8MM MMM (88) 88 88 88 [‌88‌]
eMe MMMe8 MMM (8) 888 88 88 [‌88‌]
Me MMMe8 MMM (88) 88 88 88 [‌88‌]
Me MMMe8 MMM (88) 88 88 88 [‌88‌]
(MM8)8Me MMMe8 MMM (88) 88 88 88 [‌88‌]
Me 8-MeMM8M8 MMM (88) 88 88 88 [‌88‌]

e Mee eeee eee eeeeeeee eeeeeeeeeee.

Mee eee eeeeeeeeeee ee eeeeeeee eeeeeeeee eeeeee eeee eeeeeeeeeeeeeeeeee eee eeeee eeeeeeeee eeeeeeeeeee, e eeeeeee eeeeee eeee M,M-eeeeee eeeeeee eee eeee eeeeeeee (Meeeee 88). Mee eeeeeeeeee eeeee eeeeeeeeee eeeeee eeeeeee ee eee eeeeeeee, eeeeeeeeeeeeeeeee eee 8-eeeeeeeeeee, eee eeee ee eeeeee eee eeee ee eee eeeeeee eeee ee eee eeeeeeeeee eeeeeeee eeeeeee.[‌88‌]

Meeeee 88 Meeeeeeee ee e 8-Meeeeeeeeeeeeeeeeeeee Meeeee[‌88‌]

Meeeeeeeeeeee(8-eeeeeeeeeee)eeeeeeee eeeeeee ee eeeee ee ee ee eeeeeeeee eeeeeeee eee eee eeeee-eeeeeeeee, eee-eee eeeeeeee ee eeeeeeeee, eeeeeeee eeeeee, eee eeeeeeeee eeeeeeeee ee eeeeeeeee eeeeeeeeeeeeeee ee eeeeeee 8-eeeeeeeeeeeeeeeeeeeeee ee eeee eeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeee-Meeeeeeee Meeeeeeee ee 8-Meeeeeeeeeeeeeeeeeeeee Meeeeeeee ee Meeeeeeeeeeee(8-eeeeeeeeeee)eeeeeeee Meeeeee[‌88‌]

8-Meeeeeeeeeeeeeeeeeeeeeeeee eee eeeeeeee ee eeeeeeeee eeeee ee e eeeee-eeeeeeeee eeeeeeee ee eeeeeeeee, 8,8-eeeeeeeeeeeeeeeee, eee eeeeeeeee eeeeeeeee/eeeeeeeeeeeeeeeeeeeee, ee eee eeeeeeee ee e eeeeeee eeeeeeeeeee eeeeeeee (Meeeee 88).[‌88‌] Meee eeeeeeeee eeeee ee eeeeeeeee eee eeee eeeeeeeee. 8-(Meeeeeeeeeee)eeeeeeeeeeeeeeeee eee eeeeeeeee eeeeeeee eeeee M-eeeeeeeeeeeeeeeeeee eeeeeee ee eee eeeeeeeee eee eeeeeeeeeeee eeeeee eeee eee eee eeeeeeeeeeeeeeeeeeeee (Meeeee 88).

Meeeee 88 Meeeeeeee ee 8-Meeeeeeeeeeeeeeeeeeeeeeeee eee 8-(Meeeeeeeeeee)eeeeeeeeeeeeeeeee Meeee Meeeeeeee Meeeeeeee/Meeeeeeeeeeeeeeeeeeee ee Meeeeeeee Meeeeeeee/Meeeee Meee[‌88‌]

Meeeeee eeeeeeee 8-eeeeeeeeeeeeeeeeeeeeeeeeee eee eeee ee eeeeeeee ee eeee ee eeeeeeeee eeeeee ee eeeee-eeeeeeeee eeeeeeee eeeee eeeeeeee eeeeeeeeeeeeee eeeeeeeee eeee e eeeeeee eeeeeeeeeee/eeeeeee eeeee (MMMM) eeeeeeee (Meeeee 88).[‌88‌] Meeeeeeee eeeeeeeee eee eeee eeeeeeee eeee eeeeeeee eeeeeeeee eee eee eeeee-eeeeeeeee-eeeeeeee eeeeeeee, ee eeeeeeeeeeee ee e eeeeeeeeeee eeeeeeee eeee 8-eeeeeeeeeeeeee eee eeeeeeee-8-eeeeeeeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeee 8-Meeeeeeeeeeeeeeeeeeeeeeeee ee Meeeeee Meeeeeeeeee/Meeeeee Meeee Meeeeeeee Meeee-Meeeeeeee Meeeeeee[‌88‌]

Meeeeeeeeeeeeeeee eee eeeeeeee ee eee eeeeeeee ee eeeeeeee eeeeeeeeeee eeee eeeeeee-eeeeeeeee eeeee eeeee eee eeeeeeeee (Meeeee 88).[‌88‌] Meeeeee-eeeeeeee eeeeeeee-eeeee eeeeeeeee ee eeeeeeeeeeeeeeeeeee ee eeee eeeeeeee.[‌88‌]

Meeeee 88 Meeeeee-Meeeeeeee Meeeeeeee ee Meeeeeeeeeeeeeeee[‌88‌]

8-Meeeeeeeeeeeeeeeeeeeee 8 eee eeeeeeeeeee ee eee eeeeeeeeeeeeeeeeeeee eeeeeeee ee eeeeee eeee eee MM eeeee ee eeeee eeeeeeeeeeeeeeeeeeeee ee 8888°M eeee 8e ee eeeeee eeeeeeeeeeee eeeee (Meeeee 88).[‌88‌] Mee eeeeeeeeeeeeee eeeeee ee eee eeeeeeee, eeeeeeeeeee ee 88M eee 8MMMM, ee eeee ee ee MMMM, eeeeeeee eeee eee eeeeeeee eeeeeeee eeee e eeeee eeeeee ee eeeeeeeeeeeeeeeeeeee. Mee eeeeeeeeeeeeeeeeeeee ee eeeeeeee eeeeeee eeee ee eeeee eeeeeeeeeee ee eee eeeee eeeeeeeee, ee eeeeeee ee e eeee eeeeeeeeeee, ee e eeeeee ee eeeeee eeeeeeeeeeeeee.

Meeeee 88 Meeeeeeee ee 8-Meeeeeeeeeeeeeeeeeeeee ee Meeeeeeeeeeeeeeeeeee ee Meeeee[‌88‌]

M,M-Meeeeee 8-(8-eeeee-8,8,8,8-eeeee-M-eeeeee-β-M-eeeeeeeeeeeeee)eeeee-8-(8-eeeee ee 8-eeeeeeeeeeeee)eeeeeeeeeeeeeeeeee eee eeeeeeee ee eee eeeeeeee eeeeeeeee ee eeeeeee eeeeeeeeeeee ee eeeeee, eeeee eee eeeeeeeeeeee eeeeeeee ee 8-eeeee-8-eeeeeeeeeeee (eeeeeeeeeee) eee eeeeeeee eeeeeeeee.[‌88‌]

Meeeeeee eeeeeeee ee eeeeeeee 8 eee 8, eeeeeeee eeee eeeeeeeee eee eeeeeeee, ee e eeeeeeeeee eeee ee eeeee, eeee eeeeeeeeeeeeeeee 8 ee eeee eeeeeeeeeee eeeeeee eee(α-eeeeeeeeee)eeeeeeeeeeeeeeeee 8 eee 8, eeeeeeeeeeee (Meeeee 88).[‌88‌] Mee eeeeeeeeee eeeeeeee ee eeeeeeeeee(M) eeee eeee eeeeeee eeeeeee eeeeeeeeee MMMM/MMMM, MMMM/MMMM, MMMM/MMMM, eee MMMM/MMMM, eee eee eeee eeeee, MMMM eee MMMM, eeeee M eee M eeeeeeeee eeee eee eeeee eeeeeeeeee ee eee eeeeeeeeeeeeeeee eeeeeee eeeeeeeeeeeeeeeee eeeeeeeee, eeeeeeeeeeee, eee M eee M eeeeeeeee eee eeeeeeee eeeeeeeeeeeeee ee eee M-eeeeee eeeeeeeeeee eeeeee eeeeeee. Mee eeeeeeeee eeeeeeeeee ee eee(α-eeeeeeeeeeeeeeeeeeeeee) 8 eee 8 eeee eeeee ee eeeeeeeeeeee eeeee eee(eeeeeeeeeeeeeeeeeee eeee eeeeeeeeee), e.e. 88. Meeeeeeeee eeeeeeeeee eeeee eeeeee eeeeeeeeee eeeeeee eee eeee eeeeeeeeee eeeee, e.e. 88.

Meeeee 88 Meeeeeeeeee eee Meeeeeeeee ee Mee(α-eeeeeeeeee)eeeeeeeeeeeeeeeee[‌88‌]

Mee eeeee eeeeeeeeeeeeeeee eeeeeeeee ee eeeeeeeeeee 8-eeeeeeeeeeeeeeeeeeee eeeee ee eeeeeee eee ee eee eeeeeeee ee eeeee eeeeeeeeeeeeeeeee ee eeeeee eeeeee ee eee eeeeeeee ee e eeee ee eeeeeeee. Mee eeeeeeee eeeeeeee ee eee MM eeeee ee eee eeeeeeeeeee ee eee M=M eeee eeeeeee ee e eeeeeee ee eee eeeeeeeeeeeeee eeeee eee ee eee eeeeee ee eee eeeeeeeee eeeeeeeeeee ee eee eeeeeeeee eeeeee eeeeee ee eee M=M eeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeeeeeeee Meeeeeeee ee Meeeee 8-Meeeeeeeeeeeeeeeeeee Meeee[‌88‌]

Mee eeeeeeee ee M-eeeeeeeeeeeee-8-eeeeeeeeeeeeeeeee 88 eeee eeeeeee eeeeeeeeeeee eeeeeee eeeeeee, eeeeeee 8-(8-eeeee)-8-(8-eeeeeeeeeeeeeeee)eeeeeeeeeeeeeeeeee 88, ee eeeeeeeeeeeeee eeeee (Meeeee 88).[‌88‌] Mee eeeeeeeeeeeeeeeeeeee eeeeeeee [eeeeeeeeeee eeeeeeeee ee (M,M)-88 eeee (M)-88] ee eeeeeeeee ee Meee'e eeee, ee eeee ee ee ee eeeeee eee eeeeeeeeeeeee eeeeeeeeeeee.

Meeeee 88 Meeeeeeeeeeeeeee Meeeeeeee ee Meeeee 8-Meeeeeeeeeeeeeeeeeeeee[‌88‌]

Meeeeeeeeee eeeeeee ee eeeeee eeeeee ee eee eeeeeeee eeee ee eee eeeeee eeee eeee eeee eeeeeee ee eeeeeeeee eee eeeeee ee eee eeeeeeeeeee eeeeeeee eee M,M-eeeeee eeeeee eeeeeeeee; eee eeeeeeee eeeeee ee eeee eeeeeeee-eeeeeeeeeee eeeeee eeee e eeeeeeeeee eeeeee ee eeeeeeeee ee eee eeeeeeeee eeeeee.[‌88‌]

Meeeeee (eeeeeeeeeeeee)eeeeeeeeeeee eeeeeeee eeeeee eeee eeeeeee eeeeeeeeeee ee 888°M eeeee M-(eeeeeeeeeeeeeeeeeeeeeeee)eeeeeeeeeeeeeeeee eeeeeeee eeeeee ee 88% eeeee eee ee eeeeeeee ee eee MM eeeee ee eee eeeee eeeee. Mee eeee eeeeeeee eeeeeeee eeee eee(eeeeeeeeeeeeee) eeeeeeeeeee eeeeeeee ee eeee M-{eee[(eeeeeeeeeeeeeee)eeeeeeeeee]eeeeee}eeeeeeeeeeeeeeeee eeeeeeee eeeeee, eeeee ee eeeeeee eeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeee eeee. Me eeeeeeeeee eeeeeeee eeee eee eeeeeeee eee eeeee M,M-eeeeee eeeeeeeeeee.[‌88‌]

Meeeeeeee ee eeeeeee 8-eeeeeeeeeeeeeeeeeeeeee eeee ee eeeeeeeeeeeee eeeee eeeee ee eeeeeeeeee eeeeeeee ee eeeeeeee ee eeeeeee eeeeeeeeeeee ee eeeeeeeee eeee ee M-eeeeeeeeeee eeee eee ee eeeeeee ee eeeeeee eeeeeeeeeeee.[‌88‌,‌88‌] Meeeee 88 eeeee eee eeeeeeee eeeee M-eeeeeeeeeeeeeeeeeeeeeee.

Meeeee 88 Meeeeeeee ee 8-Meeeeeeeeeeeeeeeeeeeee eee Meeeeee Meeeeeeeeee Meeeeeee ee M-Meeeeeeeeeeeeeeeeeeeeee[‌88‌]

Me ee eeeeeeee eeeeeeeee eeeeee, 8-eeeee-8-eeeeeeeeeeeeeeeeeeeee eeeee eee eeeeeeee ee eee eeeeeeee ee eeeeeee eeeeeeeeeee eeee eeeeeeeee eeee ee 8-eeeeeeeeeeeeeeeee M-eeeeeeeeee ee M-eeeeeeeeeee ee eeeeeee.[‌88‌]

Meeeeeee eeeee-eeeeeeeee eeeeeeee ee e MM eeeee ee eeeeeeeeee eeeeeeeee eeee eeeeeeeee eee eeeeee ee eeeeeee eee ee eeeee eeeeee eeeeeeeeeeeeeeee.[‌88‌] Me eeeee ee eeeeeeeee eee ee eeee ee eee eeeee eeeeeeeee (Meeeee 88).

Meeeee 88 Meeeeeee ee Meeeee Meeeeeeeeeeeeeee eeee Meeeee eee Meeeeeeeee Me Meee 8-Meeeeeeeeeeeeeeeeeeeee[‌88‌]