通过去对称缩醛化/迈克尔串联反应立体选择性合成二氧戊环和恶唑烷。
Stereoselective Synthesis of Dioxolanes and Oxazolidines via a Desymmetrization Acetalization/Michael Cascade.
作者信息
Rubush David M, Rovis Tomislav
机构信息
Colorado State University, Department of Chemistry, Fort Collins, CO 80523.
出版信息
Synlett. 2014 Mar;25(5):713-717. doi: 10.1055/s-0033-1340669.
Abstract
The desymmetrization of -quinols using a Brønsted acid catalyzed acetalization/Michael cascade was achieved in high yields and diastereoselectivities for aldehydes and imines. Use of a chiral Brønsted acid allowed for the synthesis of 1,3-dioxolane and 1,3-oxazolidine products in modest enantioselectivity.
摘要
使用布朗斯特酸催化的缩醛化/迈克尔串联反应实现了对 - 喹诺醇的去对称化，对于醛和亚胺，该反应能以高收率和非对映选择性进行。使用手性布朗斯特酸能够以适度的对映选择性合成1,3 - 二氧戊环和1,3 - 恶唑烷产物。
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Chem Commun (Camb). 2012 May 25;48(42):5076-8. doi: 10.1039/c2cc31602a. Epub 2012 Apr 16.
3
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