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36.10.1.1.14 Method 14: Synthesis of β-Amino Alcohols by Aminohydroxylation of Alkenes

DOI: 10.1055/sos-SD-036-00701

Bingham, M. J.; Greaney, M. F.Science of Synthesis, (2008361005.

The direct cis-aminohydroxylation of alkenes using imido osmium compounds was introduced in 1975 by Sharpless and co-workers as an aza analogue of cis-dihydroxylation.[‌208‌] Initially, stoichiometric amounts of preformed tertiary-alkyl imido osmium complexes were used to give cis-amino hydroxy osmate esters, necessitating a separate reductive cleavage step. The reaction was soon rendered catalytic in osmium by using chloramine-T [sodium chloro(tosyl)amide] to regenerate the imido osmium complex, resulting in a catalytic, racemic protocol for the synthesis of vic-tosylamino alcohols (Scheme 32).[‌209‌]

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Mee eeeeeeeee eeeeeeeeeeeeeeeeee eeeeeeeee eeee eee eeeeeeeee eeeeeeee eeeeeeeee eeeeeee ee ee eeeeee eeeeeee, eeee ee eeeeeeeee eeeeee {M8[MeM8(MM)8]}, e eeeeeeeeeeeeee eeeeeeee ee e eeeeeee-eeeee eeeeeee eeee ee eeeeeeeeee-M eeeeeeeeee, eee e eeeeee eeeeee eeee ee eeeeeee eeeee ee e Meeeeeee eeeeeeee eeeeeeeee. Meeeeeee eeeeeeeeee-M eee eeee eeee eeee eeeee eeeeeee ee eeeeeeeee eeeeeeeeeeeeeeeeeee, eee eeeeeeeeeeeeeeeeee eeeee eeee ee eeeeeeeeee eeeeee eee eeeeeeee eeeeeeee eeeee eeeeeeeeee eee eeeeeeeeeeee, eeeeeeeeeee eee eeeeeeeeeee ee eeee eeeeeee. Me e eeeeee, e eeeeee ee eeeeeeeeeee eeeeeeee eeeeeee eeee eeee eeeeeeeeee eeeee ee M-eeeeee eeeeeeeeeee ee eeee-eeeee[‌888‌] eee eeeeee eeeeeeeeee,[‌888‌] eeee-eeeeeeeeeeeeeeee,[‌888‌] eeeeeee eeeeee,[‌888‌] ee eeeeeeeee,[‌888‌] eeeee eeeeeee eeee-eeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeee eeee eeeee ee eeeee eeeeeeee, eeee ee eeeeeeee, eeeee, ee eeeeeeeeeeee, eeeeeee ee eeeeeee eeeeeeeeeeee. Mee eeeeee ee eee eeeeee ee eeeeeeeee, ee eee eeeee ee eeeeeeeeee eeeeeeeeee ee eee eeeeeeeeeeeeeeeeee eeeeeeee ee eeee eeeeeeeeee eeee eeee eee eee eeeeeeeee eeeeeeeeeeeeeee eeeeeee. Meee ee eeeeeeeeeeee eeeeeeee eeee eeeeeeeeeee eeeeeeeeeeeeeeee, ee eeeee eeee ee eee eeeeeeee ee eeeeeeeeeeeeeee, eee eeee ee eeeeeeeeee eeee eeeeee ee MM eee MM eeee eeeeeeeee eee eeeeeeeeeeeeeeeeee. Mee ee eee eeee eeeeee eeee eeeeeee ee eeeeee eeeeeeeeee eee eeeeeeee eee M-eeeeeeeeeeeee eeeeeee, eeeeeeeeeeee eeeee eeeeeeeeee eeeeeeee eeeeee. Meeeeeeee eeeee-, eeeee-, eee eeeeeeeeeeeeeeeeeeee eee ee eeeeeeee eeee eeee eeeeeee ee eeeeee eeeee eeeeeeeeeee eeeeeeeeee (eeeeeeeee ee 8888, Meeeeee 88 eee 88).

MMMMMM: Meeeee(MMMM) eeeee eee eeeeeeeee eeeeee eee eeeeee eeeee eee eeee ee eeeeeee eeeee eee eeeeeeee eeeeeeeeeee eee eeeeeeeee eeeeeeeeee ee eee eeeeeeee eeeeeeeeee. Meeeeeeeee eeee eeee ee eeeee eeee eeeeeeee eeeee eeeeee(MMMM) eeeee ee eeeeeeeee eeeeee, eee eeeeeee eeee eeeeeeeeeee eee eeeeeeeeeee ee ee eeeeeeeeeee (MMMM) eeeeeee eee e eeeeeeeeeeeeee eeeeeeeeeeeeeeeeee. Meeee eeeeeeeee eee eeeeeeeee eeeeeee ee eeeeeeeeee ee ee eeeeeee eeee eee eeee ee eeee, eee eee ee eeeeee ee eeeeeeee. Meee eee eeee eeeeee eeeeeeeee eee eee eeeeee eeeeeeeeeee eeeeeeeee.

Meeeee 88 Meeeeeeeeeeeeeeeee ee (M)-Meeeeeeeeeeee Meeeeee[‌888‌,‌888‌‌888‌]

Meeeeeeeeee 88

M8 M8 M Meeeeeeeee Meeee (88/88) ee (%) Meeee (%) Mee
Me MM8Me Mee M8MeM8 (8eee%), MeeMM8 (8.8 eeeee), e-MeMMe (8.8 eeeee), MeMM (8.8 eeeee), (MMMM)8MMMe (8eee%), MeMM/M8M, ee, 8.8e 88:88 88 88e [‌888‌]
8-M8MM8M8 M(M)(MMe)8 MM8Me M8MeM8 (8eee%), MeM8MMM8 (8.8 eeeee), e-MeMMe (8.8 eeeee), MeMM (8.8 eeeee), (MMM)8MMMMe (8eee%), MeMM/M8M, ee, 8.8e 8:888 88 (eee-88) 88e [‌888‌]
eMe MM8Me Mee M8MeM8 (8eee%), MeeMM8 (8.8 eeeee), e-MeMMe (8 eeeee), MeMM (8 eeeee), (MMM)8MMMe (8eee%), MeMM/M8M, ee 8:888 88 (eee-88) 88e [‌888‌]
eMe 8-MeM8M8MM8 Mee M8MeM8 (8eee%), MeeMM8 (8.8 eeeee), e-MeMMe (8 eeeee), MeMM (8 eeeee), (MMM)8MMMe (8eee%), MeMM/M8M, ee, 8e 8:8 88 (eee-88) 88e [‌888‌]
M MM8M Me M8MeM8 (8.8eee%), MeMMeMe (8 eeeee), M8M, ee, 8e 8:888 88 [‌888‌]
Me Me Me M8MeM8 (8eee%), MeMMeMe (8.8 eeeee), (MMM)8MMMMe (8eee%), e-MeMM/M8M (8:8), ee, 8.8e 88e 88 [‌888‌]
(MM8)8MMe MM8Me Mee M8MeM8 (8eee%), MeeMM8 (8.8 eeeee), e-MeMMe (8.8 eeeee), MeMM (8.8 eeeee), (MMMM)8MMMMe (8eee%), MeMM/M8M (8:8), 8°M 8:88 88 (88) 88 [‌888‌]
MM8Me Mee M8MeM8 (8eee%), MeeMM8 (8.8 eeeee), e-MeMMe (8.8 eeeee), MeMM (8.8 eeeee), (MMMM)8MMMe (8eee%), MeMM/M8M, ee, 88e 88:8 88 (88) 88e [‌888‌]

e (MMMM)8MMM=8,8-eee(8-M-eeeeeeeeeeeeeeee)eeeeeeeeeeeee.

e Meeee ee eeeee eeeeeeeeeee.

e (MMM)8MMMM=8,8-eee(8-M-eeeeeeeeeeeeee)eeeeeeeeeee.

e (MMM)8MMM=8,8-eee(8-M-eeeeeeeeeeeeee)eeeeeeeeeeeee.

e ee ee eeeee ee eee M,M-eeeeeeeeee.

e (MMMM)8MMMM=8,8-eee(8-M-eeeeeeeeeeeeeeee)eeeeeeeeeee.

Meeeee 88 Meeeeeeeeeeeeeeeee ee Meeeeeee Meeeeee[‌888‌,‌888‌‌888‌]

Meeeeeeeeee 88

M8 M Meeeeeeeee Meeee (88/88) ee (%) Meeee (%) Mee
8-eeeeee Mee MeM8 (8eee%), MeeMM8 (8 eeeee), e-MeMMe (8 eeeee), MeMM (8 eeeee), (MMM)8MMMMe (8eee%), e-MeMM/M8M (8:8), ee, 8e 8:8 >88 (eee-88) 88 [‌888‌]
Me Mee M8MeM8 (8eee%), MeeMM8 (8 eeeee), e-MeMMe (8 eeeee), MeMM (8 eeeee), (MMM)8MMMe (8eee%), MeMM/eeeeeeeee eeeeee (eM 8.88.8) (8:8), ee, 8e 8:8 88 (eee-88) 88e [‌888‌]
8-MeMM8M8 Mee M8MeM8 (8eee%), MeeMM8 (8.8 eeeee), e-MeMMe (8 eeeee), MeMM (8 eeeee), (MMM)8MMMMe (8eee%), MeMM/M8M, ee, 8e 8:8 88 (eee-88) 88e [‌888‌]
8-MeM8M8 Mee M8MeM8 (8eee%), MeeMM8 (8.8 eeeee), e-MeMMe (8 eeeee), MeMM (8 eeeee), (MMM)8MMMMe (8eee%), MeMM/M8M, ee, 8e 88:88 88 (eee-88) 88e [‌888‌]
8-(e-MeM8M)M8M8 Mee M8MeM8 (8eee%), MeeMM8 (8 eeeee), e-MeMMe (8 eeeee), MeMM (8 eeeee), (MMM)8MMMMe (8eee%), MeMM/M8M, 8°M, 88e 8:888 88 (eee-88)e 88e [‌888‌]

e 8.8 eeeee ee eeeeee eeee.

e (MMM)8MMMM=8,8-eee(8-M-eeeeeeeeeeeeee)eeeeeeeeeee.

e (MMM)8MMM=8,8-eee(8-M-eeeeeeeeeeeeee)eeeeeeeeeeeee.

e Meeee ee eeeee eeeeeeeeeee.

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Meeeeeeeeeeeee eeeeeee eee eeeeeeeee eeee eeeeeeeeee eee eee eeeeeeeee eeeeeeeeee eeeeeeeeeeeeeeeeee eeeeeeee, eeeeeeeee eeee eee eeeeee ee eeee eeeeeeeeeeeeeeeeeeee. Meeeeeeeeeeeee eeeeeeeeeeeeeeeeee ee eeeeeee eeeeeeee ee eeeeeee eee eeeeeeeee (eeeeeee) eeeee eeeeeeee, eeeee eee eeeeee eeeeeeeeeeeeeeee eeee eee eeeeeee eeeee ee eee eeee-eeeeeeeeeee eeeeee (Meeeee 88). Me eeee eeeeeeeee eee eeeeeeeeeeeeee eeeeeeee eeeeeee, eeeeeeeeeeeeeee eeee eee eeeeee eeeeeee eeeeee ee eeeeeee eeee eeeeeeeeeeeeeeeeee eee eeeeeee eee eeee eeeeeeee eeeeeee ee eee eeee ee eeeeeeeeeeeeeeee eeeeeee.[‌888‌]

Meeeee 88 Meeeeeeeeeeeeeeeee ee Meeeeeeeeeeeee Meeeeee[‌888‌‌888‌]

Meeeeee eeeeeeee eee ee eeee ee eeeeeeeeee ee eeeeeeee eeeeeeeeeeeeeeeeeee, ee eeeeeeee eeee eeeeeeeee eee eeeeeee ee eeeeeeeeeeee eeee ee eeeeeeee ee eee eeeeeeee.[‌888‌,‌888‌] Mee eeeeeee eeeeeee ee eeeee eeeeeeeee eeee eee eeeeeeeee (e.e., 88), eeeee ee eeee eeee ee eee eeeeeeeee eee eeeeeeeeeeeeee eeeeeeeeeeeeeeeeee eeeee eeeeeeee Meeeeeeee eeeeeeeee eeeeeeeeee ee eeee eeeeeeee eeee ee 88 (Meeeee 88). Mee eeeeeeeeeeeeee eeeeee ee eee eeeeeeee eeeeeee eeeeeeee eeeeeeeeeeee, eeeee ee eeeeeeeee ee eeeeeee ee eeeeeeee eeeeeeeeeeeeee eeeeeeeeeeeeeeeeeee ee eeeeeee eeeeeeee.

Meeeee 88 Meeeeeee Meeeeeeeeeeeeeeeee ee Meeeeee Meeeeeee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

(8M,8M)-8-(Meeeeeeeee)-8,8-eeeeeeeeeeeeeee (88, M8=M8=Me; M=Me); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeee eeeeee ee eeeeee eeeee ee eeeeeeeeee ee ee eeeeeee eeee eee eeee ee eeee, eee eee ee eeeeee ee eeeeeeee. Me eeee ee eeeeeee eeeee eee eeeeeeee eeeeeeeeeee eee eeeeeeeee eeeeeeeeee ee eee eeeeeeee eeeeeeeeee. Me ee eeee eeeeee eeeeeeeee eee eee eeeeee eeeeeeeeeee eeeeeeeee.

(M)-MeMM=MMMe (88.8e, 88.8eeee), eeeeeeeeee-M eeeeeeeeee (88.8e, 8.888eee, 8.8 eeeee), eee M8MeM8(MM)8 (8.888e, 8.88eeee, 8eee%) eeee eeeee eeeeeeeeeeee ee e eeee ee (MMM)8MMMM (8.88e, 8.88eeee, 8eee%) ee e-MeMM (888eM) eee M8M (888eM) ee e 888-eM Meeeeeeeee ee eeeee-eeeeeeee eeeee. Mee eeeee eee eeeeeeee ee e eeeee eeee ee ee eee eee eeeeee eee eeeeeee eee 8.8e eeeee eee eeeee eeeeeee eeee eeeee ee eeee eeeee eee eeee ee eeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeee eee eeeeee eeee eeee e eeee (~8°M) eeeeeee ee e-MeMM (8M) eee M8M (88eM); eeeee: 88.8e (88%); 88% ee (eeee ee MMM eeeeeeeeeeee eee MMMM). Meeeeeeeeee ee eeee eeeeeee eeee MeMMe (8× 88eM) ee ee ee e eeeeeeee-eeeee eeeeee eeee eeeeeeee ee eee eeeeeeeeeeeeeeee eeee eeeee eeeeeee eeeeeeeeee; eeeee: 88.8e (88%); >88% ee; ee 888888°M.

(8M)-8-(Meeeeeeeeeeeeeeeeeeeee)-8-[8-(eeeeeeeee)eeeeee]eeeeeee (eee-88, M=Mee; M8=8-MeMM8M8); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeee eeeeee ee eeeeee eeeee ee eeeeeeeeee ee ee eeeeeee eeee eee eeee ee eeee, eee eee ee eeeeee ee eeeeeeee. Me eeee ee eeeeeee eeeee eee eeeeeeee eeeeeeeeeee eee eeeeeeeee eeeeeeeeee ee eee eeeeeeee eeeeeeeeee. Me ee eeee eeeeee eeeeeeeee eee eee eeeeee eeeeeeeeeee eeeeeeeee.

MeMM (8.8e, 888eeee) eee eeeeeeeee ee M8M (888eM). M 8-M eeeee-eeeeeeee eeeee eee eeeeeee eeee 888eM ee eeee ee MeMM eeee. Mee eeeeeeeee 88eM ee eeee eee eeee ee eeeeeeee M8MeM8(MM)8 (8.888e, 8.88eeee) ee eeee e eeee eeeeeeee eeee.

M eeee ee MeeMM8 (88.8e, 888eeee) ee MeMM (888eM) eee eeeeeee eeeeeeee e-MeMMe (88.8eM, 88.8e, 888eeee) eeee eeeee eeeeeeeeeeee ee eee ee MeMM ee eee eeeeeeee eeeee eee eee eeeeeee eee eeeeeee eee ~8eee. M eeee ee (MMM)8MMMM (8.88e, 8.8eeee, 8eee%) ee MeMM (888eM) eee eeee eeeee ee eeee e eeeeeeeeeee eeeeeee. M eeee ee 8-MeMM8M8MM=MM8 (8.8e, 88eeee) ee MeMM (888eM) eee eeee eeeee, eeeeeeee ee eee M8MeM8(MM)8 eeeeeeee eeee. Mee eeeeeee eee eeeeeee ee 88°M eee 8e eeeee eee eeeee eeee eeeeee eeeee eeeeee. Me eee eeee eeeeeee eeee eeee M8M (8M) eee eeeeeeeeee ee 8°M eee 8e eeeee e eeeeeee eeeeeeeeeeee. Mee eeeeeeeee eeeee eeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeeeeeeeeeee eeee eeee M8M (888eM) eee eeee MeMM (888eM), eee eeeee eeeee eeeeee; eeeee: 88.8e (88%); eeeee (88/88) 88:88; 88% ee (eee-88).

(8MM,8MM,8MM)-8-Meeee-8-eeeeeee-8-eee-8-eeeeeeee[8.8]eeeee-8-eee (88):[‌888‌]

MMMMMMM: Meeeeeeee eeeeee ee eeeeee eeeee ee eeeeeeeeee ee ee eeeeeee eeee eee eeee ee eeee, eee eee ee eeeeee ee eeeeeeee. Me eeee ee eeeeeee eeeee eee eeeeeeee eeeeeeeeeee eee eeeeeeeee eeeeeeeeee ee eee eeeeeeee eeeeeeeeee. Me ee eeee eeeeee eeeeeeeee eee eee eeeeee eeeeeeeeeee eeeeeeeee.

M8M (8.8eM) eee eMe8MMe (8.88 eeeee) eeee eeeee ee e eeeeeee eeee ee eee eeeeeeeeeeeeeeeeeeee 88 (888ee, 8.88eeee) ee MeMM (8.8eM) eee eee eeeeeee eee eeeeeee eee 8eee. M eeee ee M8MeM8(MM)8 (8.88 eeeee) ee M8M (8eM) eee eeeeee eeeee, eee eee eeeeeee eee eeeeeee eeeee eee eeeeeeee eee eeeeeeee (MMM). Me8MM8 (~888ee) eee eeeee eee eee eeeeeee eee eeeeeee eee 88eee eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eeee eeeeee eee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeeeee eeeee 8:8) ee eeee e eeeee eee; eeeee: 88.8ee (88%).

References


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