HMPA promotes retro-aldol reaction, resulting in syn-selective addition of lithiated 1-naphthylacetonitrile to aromatic aldehydes

被引：28

作者：

Carlier, PR ^{[1
]}

Lo, CWS ^{[1
]}

Lo, MMC ^{[1
]}

Wan, NC ^{[1
]}

Williams, ID ^{[1
]}

机构：

[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 16期

关键词：

D O I：

10.1021/ol006099w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] In HMPA-THF solution, lithiated 1-naphthylacetonitrile undergoes highly syn-selective addition to aromatic aldehydes, providing the first access to such syn-aldols. Syn-selectivity is also observed with two other arylacetonitriles, Aldolate equilibration and crossover experiments demonstrate that HMPA promotes retro aldol reaction and that aldol diastereoselectivity under these conditions is thermodynamically controlled.

引用

页码：2443 / 2445

页数：3

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