通过[4 + 4]环加成-跨环环化反应合成多喹烷。

Polyquinanes by [4 + 4] cycloaddition-transannular cyclization.

作者信息

Ader T A, Champey C A, Kuznetsova L V, Li T, Lim Y H, Rucando D, Sieburth S M

机构信息

Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794-3400.

出版信息

Org Lett. 2001 Jul 12;3(14):2165-7. doi: 10.1021/ol016076x.

DOI:10.1021/ol016076x

PMID:11440570

Abstract

[reaction: see text] Photocycloaddition of 2-pyridones yields a rigid polycyclic product containing a 1,5-cyclooctadiene. The cis isomer, with the alkenes in close proximity, undergoes a transannular reaction when treated with chlorine to give a polyquinane product. The chlorination reaction involves migration of an amide nitrogen and forms a single isomer, generating eight stereogenic centers in two steps.

摘要

[反应：见正文] 2-吡啶酮的光环加成反应生成一种含有1,5-环辛二烯的刚性多环产物。顺式异构体中烯烃彼此靠近，用氯处理时会发生跨环反应，生成多喹烷产物。氯化反应涉及酰胺氮的迁移，形成单一异构体，分两步生成八个立体ogenic中心。