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40.1.1.5.4.4.3 Method 3: The Mitsunobu and Related Reactions

DOI: 10.1055/sos-SD-040-00344

Lawrence, S. A.Science of Synthesis, (200940552.

The Mitsunobu reaction enables a hydroxy group to be replaced by a wide range of nucleophiles.[‌159‌,‌271‌,‌272‌] Although the major application of the Mitsunobu reaction is the inversion of secondary alcohols, it has also been extended to the general synthesis of amines from alcohols.

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Meeeee 88 eee Meeee 8 eeee eeee eeeeeeeeeeee ee eee Meeeeeeee eeeeeeee eeeee eeeeeeeeeee eee eee eeeeeeeee ee eeeeee 888 eee eeeeeeeee eeeeeeeeeeee 888.[‌888‌,‌888‌]

Meeeee 88 Meeeeeeee ee ee Meeee ee Meeeeeeee Meeeeeee Meeee Meeeeeeeeee[‌888‌]

Meeee 8 Meeeeeeee ee Meeeeee Meeeee ee eee Meeeeeeee Meeeeeee[‌888‌]

M8MM Meeee (%) Mee
888 888
88 88 [‌888‌]
88 88 [‌888‌]
88 88 [‌888‌]
88 88 [‌888‌]

Meeeeeee ee eeeeeee eeeeeeeeeeeeeeee Meeeeeeee eeeeeeeee ee eeeeeeeeeee eeee eeeeeee eeeeeeee eeeeeeee eeeeeeeee eee eeeeee eeeeeeeeee-eeeee eeeeeeeeee eeeeeee 888 ee eeeeeeeeeee eeee eeeeeee eeeeeeeeeeeeeeee eeee eeeeeeee eeeeee ee eee eeeeee 888, eeee eeee eee eeeeeeeeeeeeeeeeee (88%) (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeeeeeeee Meeeeeeee Meeeeeeee ee Meeeee[‌888‌]

Mee eeeeeeeeeee ee M-eeeeee-8-eeeeeeeeeeeeeeeeee eee M-(eeee-eeeeeeeeeeeeee)-8-eeeeeeeeeeeeeeeeee eeeee Meeeeeeee eeeeeeeeee eee eeeeee eeeeeeeee eeeeeeeeee eee eeee eeee eee eeeeeeeeeeee eeee eeee eeeeeee eeeeeeeeee eeeeee eeeeeeeeeeee eeeeeeeeee (Meeeee 88; ee. Meeeeee 88.8.8.8.8.8).[‌888‌] Meeeeeeeeeeeee eeeeeeeee eeee 8-eeeeeeeeeeeeeeee eee -eeeeeeeeee ee 88 eee 88% eeeee, eeeeeeeeeeee, eeee eee eeeeeeeeeeeee M-eeeeeeeeee eeeeeeee. Me eee eeee ee M-(eeee-eeeeeeeeeeeeee)-8-eeeeeeeeeeeeeeeeee eeeeeeeee eeeeeee ee eee eeeeeeee eeeeeeeeee eeeeee ee eeeeeeee (Meeeee 88). Me ee eeeee eeeeee eeee 8-eeeeeeeeeeeeeeeeee eeeeee ee eee eeeeee ee eee Meeeeeeee eeeeeeee eeeee ee eeeeee eeee eeeeeeeeeeeeeeeeee ee eeee e eeeeeeeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeee Meeeeeeee Meeee 8-Meeeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 Meeee Mee
Me Me 88 [‌888‌]
(MM8)8Me Me 88 [‌888‌]
(MM8)8MMMe Me 88 [‌888‌]
Me 88 [‌888‌]
Me 88 [‌888‌]
Me 88 [‌888‌]
(MM8)8Me Mee 88 [‌888‌]
(MM8)8MMMe Mee 88 [‌888‌]
MMMe(MM8)8Me Mee 88 [‌888‌]
(M)-(MM8)8MM=MMMe Mee 88 [‌888‌]
MM8MM=MMe8 Mee 88 [‌888‌]
MMMe(MM8)8MM=MM8 Mee 88 [‌888‌]

M-Meeeeeeeee eeeeeee 888 eeeeeeee eeeee Meeeeeeee eeeeeeeeee ee eeee eeeeeeeeeee eeee eeeeeeeeee 888 (Meeeee 88).[‌888‌] Meeeeeeeeee ee eee eeeeeeeeeee eeeeeeeee eeeeeee ee eeee ee eeeeeeeee eeee eee eeeee.

Meeeee 88 Meeeeeeee ee e Meeeeeeeeee Meee Meeeeeeeee ee Meeeeeeee Meeeeeee[‌888‌]

Me e eeeeeee eeeeee, M-eeeee-8,8,8-eeeeeeeeeeeeeeeeeeeeeeeeeeee eeeee eeee eeeeeeee eeeee Meeeeeeee eeeeeeeeee ee eeee eeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee Meeeeeee ee Meeeeeeeeeeeeeeeeeeeeeeeeeee eeee Meeeeeee[‌888‌]

M eeeeeeeeee ee eee eeeeeeee ee M-eeeeee-8-eeeeeeeeeeeeeeeeee (888, M=Me) eee 8,8,8-eeeeeeeee-M-eeeeeeeeeeeeeeeeeeeeeeee (888, M=Me) eeee eeeeeee eeeeeeee eeeee eeee ee eee eeee ee eeeee eeeeeeee, eee eeeeee ee eee eeeeeeeee eeeeeeee 888 eee eeeeee eeee eee eeeeeeeeeeeeeeeeeeeeeeeeeee ee eeeeeeee (Meeeee 88).[‌888‌] Me ee eeeeeeeeeee ee eeee eeee eeee eeeeeeeeee ee eeee eeeee eeee M-eeeeee-8,8,8-eeeeeeeeeeeeeeeeeeeeeeeeeee eee M-eeeeee-8-eeeeeeeeeeeeeeeeee eee eeee, eeee eee 8-eeeeeeeeeeeeeeeeee eeeeee eeeeee eeeeee ee eee eeeeeeeee eeeeeeee ee eeee eeeee.

Meeeee 88 M Meeeeeeeee ee 8-Meeeeeeeeeeeeeeeeee eee Meeeeeeeeeeeeeeeeeeeeeeeeeee ee eee Meeeeeeee Meeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M Meeee (%) Mee
Me Me 88 [‌888‌]
Me Me 88 [‌888‌]
eMe Me 88 [‌888‌]
eMe Me 88 [‌888‌]
(MM)8MM(MM)Me Me 88 [‌888‌]
(MM)8MM(MM)Me Me 88 [‌888‌]

Mee 8-eeeeeeeeeeeeeeeeeee eeeee (Me ee eeeee) eeee ee eeee e eeeeeeeeee eee eeeeeeeeee eeeee eee eeeeee, eee ee eeeeeee eeeee eeeeeeeeee eeee eeeeeeeeee.[‌888‌] Meee eeeeeee eeeeee 888 (M8=M) eee eeeeeeeee eeeeee 888 [M8=(MM8)8Me] eee ee eeeeeeee eeee eeeeeeee eee eee eeeeeeeeeeee 888 eeeee Meeeeeeee eeeeeeeeee eeeee 8-eeeeeeeeeeeeeeeeeeeeeee ee M-eeeee-8-eeeeeeeeeeeeeeeeeeeeeeee, eeeeeeeeeeee, ee eee eeeeeeee ee ee-eeee-eeeee eeeeeeeeeeeeeeee (MMMM) eee eeeeeeee(8-eeeeeee)eeeeeeeee (Meeeee 88).[‌888‌] Meee eee MeeeeeeeMeeeeeeee eeeeeeeee[‌888‌] ee ee eeeeeeee ee eeeeeee e eeeeeee eeeeeee eeee e eeeeeeeee eeeeeee eeeee eeeee eeeeeeeeeeee eeee eeeeeeeeee.

Meeeee 88 Meeeeeeee Meeeeeee ee Meeeeeee eeee 8-Meeeeeeeeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M8 Meeee (%) Mee
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Me M M 88 88 [‌888‌]
8-MeMM8M8MM8 M M 88 88 [‌888‌]
8-M8MM8M8MM8 M M 88 88 [‌888‌]
MM=MMMe M M 88 88 [‌888‌]
Me M M 88 88 [‌888‌]
MMMeMe M M 88 888 [‌888‌]
MMMe M M 88 88 [‌888‌]
Me Me M 88 88 [‌888‌]
Me Me M 88 88 [‌888‌]
Me M (MM8)8Me 88 88 [‌888‌]
Me M (MM8)8Me 88 88 [‌888‌]
Me Me (MM8)8Me 88 88 [‌888‌]
Me Me (MM8)8Me 88 88 [‌888‌]

Meeeeee-eeeeeeeee 8-eeeeeeeeeeeeeeeeeeeeeeee, e.e. 888, eeee eeee eeee ee eeeeeeeeee Meeeeeeee eeee eeeeeeeee ee eeeee ee eeeeeeeeee (Meeeee 88).[‌888‌,‌888‌] M eeeeeee ee eeeeeeeeee eee eee eeeeeeeee eeee eeee eeeeeeee ee eeee eeeeeee.[‌888‌‌888‌]

Meeeee 88 Meeee-Meeee Meeeeeeee Meeeeeeee ee Meeeeeeeee[‌888‌]

Meeeee eee eeee ee eeeeeeeeeee eeeeeeeeee eee eee Meeeeeeeee eeeeeeeee ee eeeeee (eee Meeeeee 88.8.8.8.8.8.8), eeeee eee ee eeeeee ee eeee eeeeee eeeee eeeeeeeee eeee ee eee Meeeeeeee eeeeeeee.[‌888‌] Mee Meeeeeeeee eeeeeeeee eee ee eeeeeeee eeee eee Meeeeeeee eeeeeeee ee e eee-eee eeeeeeeee ee eeeeee eee eeeeeeeee ee eeeeeee eeeeee eeee eeeeeee eeeeeeee eee ee eeeeeeeeeeee eeeee ee eeeeeeee ee eeee eeeeee. Meee eeeeeeeee eeeeeeee eeeeeeee eeeeeeee eeee eeeeeeeee eeee, eeeeeeeeeee eeeeeeeeeeeeeeee (MMMM), eee eeeeeeeeeeeeeeeeee ee eeeeeeeeeeeeeee eeeeeeee, eeeeeeee ee eeeeeeeee eeee eeeeeee eeeeeeeeeeeeeeeeee eee eeee eeeeeeeeee (Meeeee 88).[‌888‌] Meee eee eeeeeeee ee eeeeeee ee eeeeeeeeee eeeeee eeeeeeee, ee eeee eeeee eeeee eeeeeeeee ee eeeeeeeeeeeeeee ee eeeeeeee, eee eeee eeeeee (M)-eeeeeeeee ee eeee, eeeeeee eeeeeee ee eeeeeeee. Me ee eeeeeeee eeee eeeeeeeeeeee eeeeee eee ee eee eeeeeeeee ee e eeeeeeeeee eeeeeeeee eeeeee eeeeeeeee ee eee eeeeeeeeeeee eeeee.

Meeeee 88 Meeeeeeee ee Meeeee eeee Meeeeeee eee e MeeeeeeeeeMeeeeeeee Meeeeeeee[‌888‌]

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Meeeee 88 Meeeeeeee ee Meeeeee-Meeee Meeeee[‌888‌]

Mee eeeeeeeee ee eeeeeeee 888 eeee eeeeee eeeee eee eeeeeee eeee 8 eeeeeeeeeee ee eeeeeeeeeeeeeeeeee ee e eeeee eeeeeee (eeeeee eeeeeeeeeeeee/eeeeeeeeeeeeeeeee 8:8) ee 88°M eeeeeee eee eeeeeeeee ee e eeeee ee eeeeee 888 (8888%) ee e eee-eeeee eeeeeeee. Meeeeeeee eeee eeeeeee eeeeeeee eeee 88eeeee eee eeeeeeeee eeee eeeeeeeee eeeeeeee eeee 888eeeee.[‌888‌] Me eeee 8 eeeeeeeeee ee eeeeeeeeeeeeeeeeee ee eeee, eee eeeee eeeee 888 ee eeeeeeee (Meeeee 88).

Meeeee 88 Meeeeeeee ee Meeeee eeee Meeeeeee eee Meeeee[‌888‌]

Meeeeeee(eeeeeeeeeeeeee)eeeeeeeeeee (888) eee 8-eeeeeeeeeeeeeeeeee eeeee eeee eeeeeee eee eeeeeeeee eeeeeeee ee e Meeeeeeee-eeee eeeeeeee ee eeee eeeeeeeeeeee 888, eeeee eee ee eeeeeee eeee eeeeee eeeeeeeeeeeee ee eeee eee eeee eeeeee 888 (Meeeee 88).[‌888‌] Meeee eeeeeeee eeee eeeeeeeeeeeee eeeeeeeeeeee eee eeeee eeeeeee eeeeee, eee eeeeeee eee eeeeeeee eeeeeeee eeeeee ee e eeeeeeeeeee eeeeee ee eeeeee eeeeeeeeee ee eeeeeeee eee ee eeeeeeee ee eeeeeee eee eeeeeeeee eeeeee eee eeeeeeee.

Meeeee 88 Meeeeeee(eeeeeeeeeeeeee)eeeeeeeeeee-Meeeeeee Meeeeeeee ee Meeeeeee[‌888‌]

Meeeeee eee eeeeeeeee eeeeee eeeee eeee eeeeeeee 888 ee eeeeeeeee eeeeeeeeeeeeeee, ee eee eeeeeeee ee eeeeeeeeeeeeeeeeee eee M-eeeeeeeeeeeeeeee, ee eeeee eeeeeeeee eee eeeeeeee eeeeee 888, eeeeeeeeeeee (Meeeee 88).[‌888‌] Mee eeeeeeee eeeeeeee eee eeeeeeeeeeeeeeeee eeee eeeeeeeeeeeee eee ee eeeeeeeee ee eeeeee eeeeeee, eeeeeee eeee eee eeeeeee eeeeeeee.

Meeeee 88 MeeeeeeeeeeeeeeeeeM-Meeeeeeeeeeeeeee-Meeeeeee Meeeeeeee ee Meeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M8 Meeee (%) Mee
Me Me Me 88 [‌888‌]
Me Me Me 88 [‌888‌]
Me (MM8)8 88 [‌888‌]
Me (MM8)8 88 [‌888‌]
Me (MM8)8M(MM8)8 88 [‌888‌]
Me e-Me M 88 [‌888‌]
(MM)8Me Me Me 88 [‌888‌]
MM8MMM Me Me 88 [‌888‌]
(MM8)8Me Me Me 88 [‌888‌]
MMMe8 Me M 88 [‌888‌]
Me Me 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeeeeeeeeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee 8-eeeeeeeeeeeeeeeeeeeeeee (8.888e, 8eeee) ee 8-eeeee-M-(8-eeeeeeeeeee)eeeeeeeeeeeeeeeeee (8.888e, 8eeee), eeeeeeee(8-eeeeeee)eeeeeeeee (8.888e, 8.8eeee), eee eee eeeeeee (8.8eeee) eee eeeeeeeee ee eeeee MM8Me8 (88eM) eeeee M8. Me-eeee-eeeee eeeeeeeeeeeeeeee (8.888e, 8.8eeee) eee eeeee [ee eee eeeeeee eee eeeeeeeee eeeee 8-eeeeeeeeeeeeeeeeeeeeeee, eee eee eeeeeee eeee eeee 8888eee eee eeeeeeeee eeeee 8-eeeee-M-(8-eeeeeeeeeee)eeeeeeeeeeeeeeeeee] eee eee eeeeeee eee eeeeeee ee ee eee 8e. Meee, 8M MMe ee 8,8-eeeeeee (8eM) eee eeeee eee, eeeee eeeeeeee eee 8e, eeeeee eeeeeee eee eeeeeeeeee. Mee eeeeeee eee eeeeeeeee ee MM8Me8 eee eeeeee eeee 8M MMe (8 ×). Mee eeeeeee eeeee eee eeeee (MeMM8) eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee/MeMMe).

Meeeeee eee Meeeeeeee Meeeee 888; Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee eee eeeeeeeeeee 888 (8.8eeee), MeMM (8.888e, 8.8eeee), eee M8MM8 (8.888e, 8.8eeee) ee MeMM (88eM) eee eeeeeee ee 88°M eee 888e. Meee eee eeeeeeee eee eeee eeeeeeeee (MMM) eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/MeMM/MM8).

Meeeee 888; Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeee eeeee eee eeeeeee ee eeeeeee eee ee eeeeee eeeee. Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.

M eeeeeee ee eee eeeeeee 888 (8eeee), MeM8 (8.8eeee), eee Me8M (8.8eeee) ee MMe8 (MMMMMMM: eeeee)/MMM (8:8; 88eM) eee eeeeee ee 88°M eeee eeeeeeee eee eee eeeeeeee eee eeeeeeeee ee MMM. Meee eee eee eeeeeee eee eeee eeeeeeee, eee eeeeeee eee eeeeeee ee eeee ee ee eee eeeeeeee eeee M8M (8eM). Mee eeeeeeee eeee eee eeeeeee eee 88eee eee eeee eeeeeee eeee Me8M (88eM), eee eee eeeeeee eeeee eee eeeeee eeeeeeeeee eeee M8M. Meeeeeeeeee ee eee Me8M eeeeeeee ee 8°M eeeeeeeeeee eeeeeeeeeeeeeee ee Me8MM, eeeee eee eeeeeee ee eeeeeeeeee. Mee eeeeeeee eee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee; eeeee: 8888%.

M-Meeeee-eeee-eeeeeeeeee (888, M8=Me; M8=e-Me; M8=M); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeee eeee ee Me8M (8.88e, 8eeee) eee MeMM (8.88e, 8eeee) ee eeeee MMM (8eM) ee 88°M eee eeeee MMM (8.88e, 8eeee) ee eeeee eeeeeeee eeee 88eee. Meeee 8eee, e-MeMM8 (8.8eM, 8.88e, 88eeee) eee eeeee ee eeeeeee ee eee eeeeeee. Mee eeeeeee eee eeeeeee eee e eee eee, eee eeee eeeeee ee 88°M eee 8e. Mee eeeeeeee eee eeeeee eee eeeeeeeee eeeee (88eM) eee eeeee eeee eeeee eeeeeeee. Mee Me8MM eee eeeeeeeeeee eeee eeeeeeeeeeee eeee eeeeeee ee eeeeeeeeee. Mee eeeee eee eeeeeeeee eeee eee eeeeeeee ee eee MMe/MeMM eeeeeeeeee eee eeeeeeeeee eeee eeeeeeeee eeeee eeeeeeee ee eeeeee (MeMM8) eee eeeeeeeeee. Meeeeee ee eeeeeeee eee Meeeeeeee eeeeeeeeeeee eeee eee eeeeeee; eeeee: 8.888e (88%).

References


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