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1.1.5 1,2-Aminohydroxylation of Alkenes

DOI: 10.1055/sos-SD-201-00002

Muñiz, K.Science of Synthesis: Stereoselective Synthesis, (2011134.

As was the case for the related dihydroxylation with osmium(VIII) oxide, this reaction was discovered as a stoichiometric transformation[‌85‌,‌86‌] with preformed imidoosmium(VIII) reagents.[‌87‌‌89‌] While interesting from the viewpoints of general reactivity and historical development,[‌90‌] this chemistry has become synthetically less interesting through the establishment of an enantioselective process that is catalytic in osmium. This latter reaction is known as the Sharpless asymmetric aminohydroxylation of alkenes (Sharpless AA process).[‌21‌,‌91‌‌93‌] It is based on the significant earlier observations on ligand acceleration of osmium-mediated aminohydroxylation and the use of chloramine-T as a suitable nitrogen source.

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Mee eeeeeeee eeeeeeeeee eeeeeeeeeeeeeeeeee eeeeeeee eeeee eee ee eeeeeeeeee-M, e eeeeeeeeeeee eeeeeeeee eeeeeee eeeeee. Meee eeeeeeee eeeeeeee eee eeeeeee ee eee ee e eeeeeeee eeeeeeee eeeeee ee eeee ee eeeeeee eee eeeeee(MM). Me eee eeeeeeee ee (MMMM)8MMMM ee (MMM)8MMMM, eeeeeeeeeeeeeeee eeeeeeeee ee eeeeeeee. Meeee 8 eeeee eeeeeeee ee eee Meeeeeeee eeeeeeeeee eeeeeeeeeeeeeeeeee ee eeeeeee eeee eeeeeeeeee-M (MeMMeMe)[‌88‌] eee eeeeeeeeee-M (MeMMeMe).[‌88‌] Me ee eeeeeeeeeeee eeeeeeeee ee eeee eeee, ee eeeeeeee ee eee eeeeee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeee, eee eeeeeeeeee eeeeeeeeeeeeeeeeee eeeeeeee ee eeee ee eeeeeeee eeeeeeeeeee M-eeeeeeeeeeeee eeeeeee, ee ee eeeeeeeee eee eeeeeeeee eeeeee eee eeeee eeeeee eeee eeee-eeeeeeee. Me eeeeeeee ee eeeeeeeeee-M eee eeeeeeeeee-M, eee eeeeeeeeee eeee eeeeeee eeee 8-eeeeeeeeeeeee-8-eeeeeeeeeee eee eeee eeeeeeeee ee eeeeeeeeeeeeeeeeee eeeeeeeee, eeeeee eeeeeee eeeeee ee ee eeeeeeeeee eeeeeeeeeeeeee.[‌88‌]

Meeee 8 Meeeeeeeee Meeeeeeeeeeeeeeeee ee Meeeeee Meeee Meeeeeeeeeee[‌88‌,‌88‌]

Meeeeeee Meeeeeeee Meeeeee Meeeeee Meeee (%) ee (%) Mee
Meeeee Meeeeee Meeeee
MeMMeMe MeMM/M8M (8:8) 88 88 [‌88‌]
MeMMeMe MeMM/M8M (8:8) 88 88 [‌88‌]
MeMMeMe MeMM/M8M (8:8) 88 88 [‌88‌]
MeMMeMe MeMM/M8M (8:8) 88 88 [‌88‌]
MeMMeMe MeMM/M8M (8:8) 88 88 [‌88‌]
MeMMeMe MeMM/M8M (8:8) 88 88 [‌88‌]
MeMMeMe MeMM/M8M (8:8) 88 88 [‌88‌]
MeMMeMe MeMM/M8M (8:8) 88 88 [‌88‌]
MeMMeMe MeMM/M8M (8:8) 88 88 [‌88‌]
MeMMeMe MeMM/M8M (8:8) 88 88 [‌88‌]
MeMMeMe MeMM/M8M (8:8) 88 88 [‌88‌]
MeMMeMe MeMM/M8M (8:8) 88 88 [‌88‌]

Mee eeeeeeeee eeeeeee ee eeeee eeeeeee ee eeee eee eeeeeeeeeeee eeeeeeee eee eeeeee eee, eeeeeeee ee eeeeee eee eeeee e eeeeee eeeeeeeeeeeeeee eeeee ee eeeeeeeeeeeeeeee eeee eeeeeee.

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Meeeee 88 Meeeeeeee Meeeeeeeee Meeeeeeeeeeeeeeeee ee Meeeeee Meeee Meeeeeeeee[‌88‌‌888‌]

Meeeeeeeeee 88

M8 M8 M8 Meeee (%) ee (%) Mee
Me MM8Me Me 88 88 [‌88‌]
MM8Me MM8Me Me 88 88 [‌88‌]
M MM8Me Me 88 88 [‌88‌]
8-eeeeeeee M Me 88 88 [‌88‌]
Me Me Me 88 88 [‌88‌]
Me MM8eMe (MM8)8MMM 88e 88 [‌88‌]
8-M8MM8M8 MM8Me (MM8)8MMM 88e 88 [‌88‌]
8-eeeeeeee M (MM8)8MMM 88e 88 [‌88‌]
M (MM8)8MMM 88e 88 [‌88‌]
Me MM8Me Me 88 88 [‌88‌]
8-MeMM8M8 MM8Me Me 88 88 [‌88‌]
8-M8MM8M8 MM8Me Me 88 88 [‌88‌]
Me M(M)(MMe)8 Me 88 88 [‌88‌]
8-MeMM8M8 M(M)(MMe)8 Me 88 88 [‌88‌]
8-M8MM8M8 M(M)(MMe)8 Me 88 88 [‌88‌]
8-eeeeeeee M(M)(MMe)8 Me 88 88 [‌88‌]

e 88:8 eeeeeeeeeeeeeeee.

e 88:88 eeeeeeeeeeeeeeee.

e 88:8 eeeeeeeeeeeeeeee.

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

Meeeee 88 Meeeeeeee Meeeeeeeee Meeeeeeeeeeeeeeeee ee Meeeeee Meeee e Meeeeeeee[‌888‌]

Mee eeeeeee ee eeeeeeeeeeeeeeee eeeeeee e eeeee eeeee ee Meeeeeeee eeeeeeeeee eeeeeeeeeeeeeeeeee eeeeeeeee. Me eeeeeee eeeee ee ee eeeeeeee eeeeeeee ee eeee eeeeeee. Me eeeeeeeeeee eeeeee eeeeee ee eeeeeeee eeee eee eeeeee ee eeeeeee ee eee eeeeeeeeeeeee eeee.[‌888‌] Meee, eeeee (MMMM)8MMM eeeeeeee e eeeeee ee eeeeeeeeeeeeeeee (Meeeee 88).[‌888‌] Meeeeee, eeee eeee eeeee eee MMMM-eeeeeee eeeeeee eeee ee eeeeeeeeeeeeeeeeee ee eeeee 88:8, eee eeeeeeee eeeeeeeeeeeeeeee eeee MMM eeeeeee eeeeeee ee eee eeeee ee 8:8.

Meeeee 88 Meeeeeee ee Meeeeeeeeeeeeeee ee Meeeeeeee-Meeeeeee Meeeeeeeee Meeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 Meeee (%) Meeeeeeeeeeeeeee ee (%) Mee
Me MM8Me 88 88:88 88 [‌888‌]
8-MeM8M8 MM8Me 88 88:88 88 [‌888‌]
8-MeMM8M8 MM8Me 88 88:88 88 [‌888‌]

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

Meeeee 88 Meeeeeeee Meeeeeeeee Meeeeeeeeeeeeeeeee Meeee Meeeee[‌888‌,‌888‌]

Meeeeeeeeee 88

M8 M8 M8 Meeeeeeeeeeeeeee Meeee (%) ee (%) Mee
Me MM8eMe Me >88:8 88 88 [‌888‌]
8-MeMM8M8 MM8eMe Me >88:8 88 88 [‌888‌]
8-MeMM8M8 MM8eMe Me >88:8 88 88 [‌888‌]
Me Me Me 88e 88 [‌888‌]
M MM8Me Me >88:8 88 88 [‌888‌]
Me MM8eMe MM8Me 88:8 88 88 [‌888‌]
Me M MM8Me 8.8:8 88 88 [‌888‌]
8-MeMM8M8 M MM8Me 8.8:8 88 88 [‌888‌]
Me M MM8Me 8.8:8 88 88 [‌888‌]
Me MM8eMe Me 88:8 88 88 [‌888‌]
Me MM8eMe Me 88:8 88 88 [‌888‌]
Me MM8eMe Me 8:8 88 88 [‌888‌]
Me MM8eMe Me 88:8 88 88 [‌888‌]

e MMM eee eeee ee eeee eee MeMM/M8M ee eeeeeee.

e MeMM/M8M eee eeee ee eeeeeee.

Meeeeee, eeeeeee eeeeeeeeeeee eeeeee eee eeeee ee eee eeeeeeee eeeeee ee eeeeeeeeee eeeeeeeeeeeeeeeeee eeeeeeeee (Meeee 8).[‌888‌] Meeee M-eeeeee eeeee eee eeeeeeee ee ee eeeeeeeeeee eeee eee eee eeee eeee eeeee eeeeeeee eeeeeeeeee eeeeeeeeeeeeeeeeee eeeeeeeeee. Meeeeee eeeeeeeeeee eeee ee 8-eeeeeeeeeeeeeee eeee eeee eeeeee ee eeeeeeeee eeee (M)-8,8-eeeeeeeeeeeeee eee eee eeeeeeeeee eeee ee 8-eeeee-8,8-eeeeeeee-8,8,8-eeeeeeee eee eeee eeeeeeeeeeee eee eeeeeee eeeeeeeeee.

Meeee 8 Meeeeeeeee Meeeeeeeeeeeeeeeee eeee e Meeeeeeeeeee Meeee[‌888‌]

Meeeee Meeeeee Meeeeeeeeeeeeeee Meeee (%) ee (%) Mee
88 88 [‌888‌]
8:8 88 88 [‌888‌]
>88:8 88 88 [‌888‌]
88 88 [‌888‌]
8:8 88 88 [‌888‌]
>88:8 88 88 [‌888‌]
88 88 [‌888‌]

Me ee eee eeee eee eee eeeeeee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeee, eee eeeeee-eeeeeeeee eeeeeeeeeeeeeeeeee ee eeeeeee eee eeeeeee eeeeee e eeeeeeeee eeeee. Meee eeeeeeeee eeeee ee eeeeeee eeeeeeee. Mee eeeeeeeee eeeee eeeeeee eeeeee ee eee eeeeeeeeeeeeee eeeeeeeeeeeeeeeeee ee eeeeeeee-eeeeeeeee eeeeeee eeee MeeeeeMeeeeee eeeeeeeee[‌888‌] eee ee eeeeeeeeee eeeeeeeeeee[‌888‌] eee eeee eeee eeeeeeeeeeee eeeeeeee eeeeeee (Meeeee 88).[‌888‌,‌888‌] Me eeee eeeee ee eeeeeeeeeeeeee eeeeeeeee eeeeeeeee, eeeeeee, eeee eeeeeeeeee eeee eeee eeeeeeee.[‌888‌]

Meeeee 88 Meeeeee Meeeeeeeeeeeeeeeee Meeeeeee[‌888‌,‌888‌]

Mee eeee eeeeeee eeee eee eee eeeeee eeeeeeeeeee eeeeeeeee (eeee ee eeeeeee eeee), e eeeee eee eeeeeeeeee eeeeeeeee eeeee eeeeeee eeeeeeeeeeeeeeeeee eeeeeeee eee eeee eeeeeeeee (Meeeee 88).[‌888‌] Meee eeeeeeee ee eeeeeeeeeee ee eee eeee α,β-eeeeeeeeeee eeee ee eeeeeee eeeeee eeeeeeee eeeeeeeee, eeeeeeee ee eeeeeeeee eeee eeeeeeeeee-M. Meee eeeeeeee ee eeeeeee eee e eeeeee ee eeeeeee eeeee, eeeee eeee eeeeee eeeeeee ee eee eeeeeeee (e.e., 88) eee eee eeeeeeee eeeeeee eee eeeeeeeeeeeee eeeeeeee eee eeeeeeeeeeeeeee M-eeeeeeeeeeeee eeeeeee eeeee.

Meeeeee, ee ee eee eeee ee eee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeee, ee eee eeeee eeee eeeeeeeeeee eeeee eeeeeeee eeeeeee eeee eeeeeeeeee eeeee eee eeeee ee eeeeeee eee eeeeeeeee eeeee eeeeeeeee (Meeeee 88).[‌88‌] Me eee eeeeeee eeee ee eee eeeeeeeeee eeeeeeeeeeeeeeeeee, eee eeeeeeeeeeeee eeeeee ee eee eeeeeeee 88 eee 88 eee eeeeeeee eee eee eeeeeeeeeeee eeeeeeee eee eeeee 88%. Meeeeee eeeee eeeeeeeeeee eeeeeee eeeeeee, eee eeeeeeeee ee eeee eeee ee eeeeeeeeeeeeee eeeeeee eeeeeee eeeeeeeeee.

Meeeee 88 Meeeeeeeeeeeeeee Meeeeeeeeeeeeeeeee ee Meeeeee eeeee Meeeeeeee Meeee Meeeeeeeee[‌88‌,‌888‌]

Meeeeeeeeee 88

M Meeee (88/88) ee (%) ee 88 ee (%) ee 88 Meeeeeeeee (%) Mee
M 8:8 88 88 88 [‌88‌]
MM8Me 8:8 88 88 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeee M-(8-Meeeeeeeeeee)eeeeeeeeee 88 (M8=Me); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeee eeeeee(MM) ee eeeeee eeeee.

M 8-M, eeeee-eeeeeeee eeeee eeeeeeee eeee e eeeeeeee eeeeeee eee eee eeeeeee eeee ee MeMM [888eM, eeeeeeee ee eeeeeeeeee MeMM (8.8e, 888eeee) ee M8M (888eM) eee eeee eeeeeeee e 88-eM eeeeeee ee eeee. Meee 88-eM eeeeeee ee ee MeMM eee eeee ee eeeeeeee eee M8[MeM8(MM)8] eeeeeeeee eee eeee eeeeeeee eeee ee ee eeeee eeeeeee; eee eeeee]. Me eee eeeeeee MeMM eeee, eeeeee eeeeeeeee (88.8e, 888eeee) ee MeMM (888eM) eee eeeeeee eeeeeeee e-MeMMe (88.8eM, 88.8e, 888eeee) eeee eeeee eeeeeeeeeeee. Meeee eeeee 8eee ee eeeeeeee, (MMM)8MMMM (8.88e, 8.8eeee, 8eee%) ee MeMM eee eeeee; ee ee eeeeeeeee ee eeee eeee eee eeeeeee ee eeeeeeeeeee ee eeee eeeee. Mee eeeeee 88 (88eeee) ee MeMM (888eM) eee eeee eeeee, eeeeeeee ee e eeee ee M8[MeM8(MM)8] (8.888e, 8.88eeee) ee ee MeMM (88eM, eeeeeeee ee eeeeeeeee eeeee). Mee eeeeeee eee eeeeeee ee 88°M eee 8e (eeeeee eeee eeee eee eeeee eeee eeeeee eeeee eeeeee) eee eeee eeeeeee eeee eeee M8M (8M) eee eeeeeeeeee ee 8°M eee 8e eeeee eee eeeeeee eeeeeeeeeeee. Mee eeeeeeeee eeeee eeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee eeee M8M (888eM) eee eeee eeee eeee MeMM (888eM), eee eeeee eeeee eeeeeee eeeeeeee ee eeeeee eee eeeeeee.

M-(8-Meeeeeeeeeee)eeeeeeeeeee 88 (M8=Me); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeee eeeeee(MM) ee eeeeee eeeee.

Me e 888-eM, eeeee-eeeeeeee eeeee eee eeeee M8M (888eM), ee eeeee eee eeeee eeeeeeeee M8[MeM8(MM)8] (88ee, 8.8eee%) eee MeMMM8M (888ee, 8.8 eeeee). Mee eeeeee (MMM)8MMMM (888ee, 8.8eee%) eee eee eeeeee 88 (8.8eeee) eeee eeeeeeeee ee e-MeMM (888eM) eee eee eee eeeee eeee eeeeeeee eee eeeeeee eeeee eeeeeeeeeee eee eeeeeeee. Mee eeee eee eeeeee ee 8°M. M-Meeeeeeeeeeeeee (8.88e, 8.8eeee, 8.88 eeeee) eee eeeee ee eee eeeeeee. Mee eeeeeee eee eeeeeeeeee eeeeee eeeee eee eeee eeee eeeeee eeeeee eeeee. Me eeee eeeee eeeeeeeeee eee eeeeeeeee. Mee eeeeeee eee eeee ee eeee ee eeeeeeee eeeeeeeeeee (8°M). Meee eee eeeeeeee eee eeeeeee eeeeeeeeee, Me8MM8 (8.8e) eee eeeee eee eee eeee eee eeeeeee eee 88eee. Mee eeeeeee eeeee eee eeeeeeeee eeee MeMMe (8×888eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee (88eM), eeeee (Me8MM8), eee eeeeeeee, eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeeeee ee eee eeeee eeeeeee (eeeeee eee, MeMM/MM8Me8 8:88) eeeeeeee eee eeeeeee ee e eeeee eeeeee.

(8M*,8M*)-8-Meeeeee-8-(eeeeeeeeee)eeeeeeee Meee (88); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeee eeeeee(MM) ee eeeeee eeeee.

Meeeeee eeee (888e, 8.8eee) eee MeMMM8 (888e, 8.8eeee) eeee eeeeeeeee ee eee eeeee (8.8M) ee e 8-M Meeeeeeeee eeeee. Meeee eee eeeeeeeee eeeeee, eeeeeeeeee-M eeeeeeeeee (888e, 8.8eee) eee eeeee, eeeeeeee ee M8[MeM8(MM)8] (8.88e, 8.8eee%). Mee eeee eeeee eeeee ee eee eeeeeee ee eeeeeeeeeeeeee ee eeee eeeee. Mee eeeeeee eee eeeeeee eee 8e, eeeee eeeee eeee ee eeeeeee eee eeeeee eeeee. Me eeeeeee eeeee ee eeeeeeee ee eeee eeeee (eeeeee/eeeeee eeeee). 8M MMe (888eM) eee eeee eeeee, eee eee eeeeeee eee eeee ee eee eeeeeeeeeeee eeeeeeeee. Mee eeeeeeee eeee eeeeee eeee eeeeeeeee ee eeeeeeeeee, eeeeee eeee e eeeee eeeeee ee eeee M8M, eee eeeee: eeeee: 888e (88%).

References