Synthesis of 2,3-anti-3,4-anti and 2,3-anti-3,4-syn propionate motifs:: A diastereoselective tandem sequence of mukaiyama and free-radical-based hydrogen transfer reactions

被引：23

作者：

Guindon, Y

Prévost, M

Mochirian, P

Guérin, B

机构：

[1] Inst Rech Clin Montreal, Bioorgan Chem Lab, Montreal, PQ H2W 1R7, Canada

[2] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

[3] Univ Montreal, Dept Pharmacol, Montreal, PQ H3C 3J7, Canada

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 06期

关键词：

D O I：

10.1021/ol025605+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Reported herein is a strategy employing a Mukaiyama reaction in tandem with a hydrogen transfer reaction for the elaboration of 2,3-anti-3,4-anti and 2,3-anti-3,4-syn propionate motifs. The mode of complexation is controlled through monodentate or chelate pathways for the Mukaiyama reaction to give access to either syn or anti aldol products, precursors of the free-radical reduction reaction. Boron Lewis acid is used to control the free-radical reaction through the exocyclic pathway.

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页码：1019 / 1022

页数：4

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