通过将乙烯基格氏试剂加成到羧酸酯中一锅法合成高烯丙基酮。

One-pot synthesis of homoallylic ketones from the addition of vinyl grignard reagent to carboxylic esters.

作者信息

Hansford Karl A, Dettwiler James E, Lubell William D

机构信息

Département de Chimie, Université de Montréal, C.P. 6128, Succursale Centre Ville, Montréal, Québec, Canada H3C 3J7.

出版信息

Org Lett. 2003 Dec 11;5(25):4887-90. doi: 10.1021/ol0359822.

DOI:10.1021/ol0359822

PMID:14653699

Abstract

Fifteen homoallylic ketones have been synthesized in 26-77% yields on treatment of aromatic, aliphatic, and alpha-amino methyl carboxylates with excess vinylmagnesium bromide and catalytic amounts of a copper salt in THF. Alpha-amino homoallylic ketones derived from N-protected alpha-amino esters possessing aliphatic and alcohol side chains were synthesized in > or =98% enantiomeric purity. [reaction: see text]

摘要

在四氢呋喃中，用过量的乙烯基溴化镁和催化量的铜盐处理芳香族、脂肪族和α-氨基甲基羧酸盐，以26%-77%的产率合成了15种高烯丙基酮。由具有脂肪族和醇侧链的N-保护α-氨基酯衍生的α-氨基高烯丙基酮，其对映体纯度≥98%。[反应：见正文]