有机催化串联杂 Diels-Alder 和 Friedel-Crafts 反应：具有支架多样性的稠合杂环的构建。

Organocatalytic sequential hetero-Diels-Alder and Friedel-Crafts reaction: constructions of fused heterocycles with scaffold diversity.

机构信息

Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.

出版信息

Org Lett. 2011 Nov 4;13(21):5874-7. doi: 10.1021/ol202492x. Epub 2011 Oct 13.

DOI:10.1021/ol202492x

PMID:21995624

Abstract

A highly enantioselective aza-Diels-Alder and Friedel-Crafts reaction sequence of N-sulfonyl-1-aza-1,3-butadienes and aliphatic aldehydes tethered to an arene motif has been developed, affording the fused chiral piperidine frameworks with a versatile scaffold diversity. A similar strategy has been applied for the construction of complex chiral tetrahydroquinoxaline structures.

摘要

发展了一种高度对映选择性的氮磺酰基-1-氮杂-1,3-丁二烯和连接芳基骨架的脂肪族醛的aza-Diels-Alder 和 Friedel-Crafts 反应序列，提供了具有多功能支架多样性的稠合手性哌啶骨架。类似的策略也被应用于构建复杂的手性四氢喹喔啉结构。