Stereoselective Synthesis of Dioxolanes and Oxazolidines via a Desymmetrization Acetalization/Michael Cascade

被引：19

作者：

Rubush, David M. ^{[1
]}

Rovis, Tomislav ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

SYNLETT | 2014年 / 25卷 / 05期

关键词：

acetals; desymmetrization; Michael addition; stereoselective synthesis; cascade catalysis; CATALYTIC ENANTIOSELECTIVE SYNTHESIS; DOUBLE-BOND ISOMERIZATION; ASYMMETRIC-SYNTHESIS; ACID CATALYSIS; CONJUGATE ADDITION; MICHAEL ADDITION; 1,3-DIOXOLANES; PEROXYQUINOLS; METATHESIS; RESOLUTION;

D O I：

10.1055/s-0033-1340669

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The desymmetrization of p-quinols using a Bronsted acid catalyzed acetalization/Michael cascade was achieved in high yields and diastereoselectivities for aldehydes and imines. Use of a chiral Bronsted acid allowed for the synthesis of 1,3-dioxolane and 1,3-oxazolidine products in modest enantioselectivity.

引用

页码：713 / 717

页数：5

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