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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