双非对映选择性超季铵乙醇酸酯醛醇反应：在多官能化内酯不对称合成中的应用

Double diastereoselective SuperQuat glycolate aldol reactions: application to the asymmetric synthesis of polyfunctionalised lactones.

作者信息

Davies Stephen G, Nicholson Rebecca L, Smith Andrew D

机构信息

The Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK.

出版信息

Org Biomol Chem. 2004 Nov 21;2(22):3385-400. doi: 10.1039/B411724G. Epub 2004 Oct 11.

DOI:10.1039/B411724G

PMID:15534718

Abstract

Polyfunctionalised lactones with up to five contiguous stereocentres may be prepared with high stereocontrol by a double diastereoselective aldol protocol with protected homochiral alpha,beta-dihydroxy- or alpha,beta-gamma-trihydroxyaldehydes and a chiral glycolate oxazolidinone, followed by subsequent O-desilylation and lactonisation.

摘要

通过双非对映选择性羟醛反应，使用受保护的同手性α,β-二羟基或α,β,γ-三羟基醛与手性乙醇酸恶唑烷酮，随后进行O-去硅基化和内酯化反应，可高立体控制地制备具有多达五个连续立体中心的多官能化内酯。