从β-四氢萘酮和α,β-不饱和醛合成 2,3,5,6-四氢-1-烷基/芳基-1H-苯并[f]色烯-3-醇衍生物。

Synthesis of 2,3,5,6-tetrahydro-1-alkyl/aryl-1H-benzo[f]chromen-3-ol derivatives from β-tetralones and α,β-unsaturated aldehydes.

机构信息

Department of Chemistry, National Taiwan Normal University, 88 Sec. 4, TingChow Road, Taipei, Taiwan 116, ROC.

出版信息

Org Biomol Chem. 2011 Nov 7;9(21):7510-6. doi: 10.1039/c1ob05966a. Epub 2011 Sep 20.

PMID:21931922

Abstract

Organocatalytic domino Michael-hemiacetalization of β-tetralones with α,β-unsaturated aldehydes is presented. Treatment of β-tetralones with α,β-unsaturated aldehydes in the presence of diphenylprolinol silyl ether gave 2,3,5,6-tetrahydro-1-alkyl/aryl-1H-benzo[f]chromen-3-ol derivatives with high to excellent chemical yields (50-99%) and high levels of enantioselectivities (up to 96% ee).

摘要

本文报道了β-四氢萘酮与α,β-不饱和醛的有机催化串联迈克尔-半缩醛化反应。在二苯脯氨醇硅醚的存在下，β-四氢萘酮与α,β-不饱和醛反应，以高至优异的化学收率（50-99%）和高对映选择性（高达 96%ee）得到了 2,3,5,6-四氢-1-烷基/芳基-1H-苯并[f]色醇衍生物。