Synthesis of (R)- or (S)-diphenylphosphinoyl hydroxy aldehydes and 1,2-diols using Mukaiyama's bicyclic aminal methodology and Sharpless asymmetric dihydroxylation

被引：12
作者：
OBrien, P [1 ]
Warren, S [1 ]
机构：
[1] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 17期
关键词：
D O I：
10.1039/p19960002129
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two different approaches to diphenylphosphinoyl hydroxy aldehydes and 1,2-diols are compared. A lengthy chiral auxiliary approach using proline-derived aminals enables hydroxy aldehydes and 1,2-diols of known absolute stereochemistry and high enantiomeric excess to be synthesised, In contrast, a much shorter asymmetric dihydroxylation route generates 1,2-diols with lower enantiomeric excesses and unexpected (in view of Sharpless's mnemonic) absolute stereochemistry. The dihydroxylation results are thus of both mechanistic and synthetic value.
引用
收藏
页码：2129 / 2138
页数：10
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