A practical stereoselective synthesis of chiral hydrobenzoins via asymmetric transfer hydrogenation of benzils

被引：185

作者：

Murata, K

Okano, K

Miyagi, M

Iwane, H

Noyori, R

Ikariya, T

机构：

[1] Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan

[2] Japan Sci & Technol Corp, CREST, Meguro Ku, Tokyo 1528552, Japan

[3] Mitsubishi Chem Corp, Tsukuba Res Ctr, Ami, Ibaraki 30003, Japan

[4] Nagoya Univ, Dept Chem, Nagoya, Aichi 4648601, Japan

[5] Nagoya Univ, Res Ctr Mat Sci, Chikusa Ku, Nagoya, Aichi 4648601, Japan

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 07期

关键词：

D O I：

10.1021/ol990226a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Asymmetric reduction of benzil with RuCl[(S,S)-Tsdpen)(eta(6)-p-cymene) in a mixture of formic acid and triethylamine proceeds with a substrate/catalyst molar ratio of 1000-2000 to give (R,R)-hydrobenzoin quantitatively with high diastereomeric (97% de) and enantiomeric purities (>99% ee), in which the benzoin intermediate with a chirally labile stereogenic center is converted to one major stereoisomer, (R,R)-product, via dynamic kinetic resolution.

引用

页码：1119 / 1121

页数：3

共 34 条

[1] Catalytic asymmetric oxidation of aryl sulfides with a Ti/H2O/(R,R)-diphenylethane-1,2-diol complex:: a versatile and highly enantioselective oxidation protocol [J].