路易斯酸模板催化的不对称狄尔斯-阿尔德反应

Lewis acid template-catalyzed asymmetric diels-alder reaction.

作者信息

Ishihara Jun, Nakadachi Shino, Watanabe Yuki, Hatakeyama Susumi

机构信息

Graduate School of Biomedical Sciences, Nagasaki University , 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.

出版信息

J Org Chem. 2015 Feb 20;80(4):2037-41. doi: 10.1021/acs.joc.5b00055. Epub 2015 Jan 29.

DOI:10.1021/acs.joc.5b00055

PMID:25621816

Abstract

An asymmetric Diels-Alder reaction of 2,4-dienols and methyl acrylate utilizing a chiral Zn(II)/Mg(II) bimetallic template with low catalyst loading was successfully achieved. The bimetallic Lewis acid template derived from (R)-5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol catalyzed the Diels-Alder reaction in the presence of molecular sieves 4 Å to afford various functionalized bicyclic γ-lactones with high enantiomeric purities.

摘要

利用低催化剂负载量的手性锌（II）/镁（II）双金属模板成功实现了2,4 - 二烯醇与丙烯酸甲酯的不对称狄尔斯-阿尔德反应。源自（R）-5,5',6,6',7,7',8,8'-八氢-1,1'-联-2-萘酚的双金属路易斯酸模板在4Å分子筛存在下催化狄尔斯-阿尔德反应，以提供具有高对映体纯度的各种官能化双环γ-内酯。