Catalyst-directed diastereoselectivity in hydrogenative couplings of acetylene to α-chiral aldehydes:: Formal synthesis of all eight L-hexoses

被引：58

作者：

Han, Soo Bong ^{[1
]}

Kong, Jong Rock ^{[1
]}

Krische, Michael J. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 18期

关键词：

D O I：

10.1021/ol8018874

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrogenative coupling of acetylene to alpha-chiral aldehydes 1a-4a using enantiomeric rhodium catalysts ligated by (S)-MeO-BIPHEP and (R)-MeO-BIPHEP delivers the diastereomeric products of carbonyl-(Z)-butadienylation 1b-4b and 1c-4c, respectively, with good to excellent levels of catalyst directed diastereofacial selectivity. Diastereomeric L-glyceraldehyde acetonide adducts 1b and 1c were converted to the four isomeric enoates 6b, 8b, 6c, and 8c, representing a formal synthesis of all eight L-hexoses.

引用

页码：4133 / 4135

页数：3

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