4-hydroxyphenylglycine-based oxazaborolidines for enantio-selective reductions of ketones

被引：11

作者：

Braun, Manfred ^{[1
]}

Sigloch, Michael ^{[1
]}

Cremer, Jens ^{[1
]}

机构：

[1] Univ Dusseldorf, Inst Organ Chem & Makromol Chem, D-40225 Dusseldorf, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 03期

关键词：

amino alcohols; asymmetric catalysis; boron; substituent effects; synthetic methods;

D O I：

10.1002/adsc.200600297

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Amino alcohols 6 featuring the diphenylhydroxymethyl group are prepared from the commercial amino acid (R)-4-hydroxyphenylglycine 3. Oxazaborolidines generated in situ from the amino alcohols 6 and borane-dimethyl sulfide serve as catalysts in enantioselective reductions of acetophenone. The para-substituents of the phenyl ring at the stereogenic carbon atom have a substantial influence on the enantioselectivity. When mediated by the nonaflate 6d, the reduction of ketones 7, 9, 11, and 13 leads to the carbinols 8, 10, 12, and 14 in 90 to 96 % ee.

引用

页码：337 / 342

页数：6

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