One-Carbon Incorporation Using Cyclobutanone Oxime Ester Enabled [2 + 2 + 1] Carboannulation of 1,7-Enynes by C–C/N–O Bond Cleavage and C–H Functionalization

A NiCl2-promoted [2 + 2 + 1] carboannulation of 1,7-enynes with internally oxidative cyclobutanone oximes to produce canyo-functionalized 4H-cyclopenta­[c]­quinolin-4-ones is disclosed. Through C–C/N–O bond cleavage and C–H functionalization, the process enables one-carbon incorporation using cyclob...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2019-12, Vol.21 (23), p.9434-9437
Main Authors: Yu, Jiang-Xi, Teng, Fan, Xiang, Jian-Nan, Deng, Wei, Li, Jin-Heng
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A NiCl2-promoted [2 + 2 + 1] carboannulation of 1,7-enynes with internally oxidative cyclobutanone oximes to produce canyo-functionalized 4H-cyclopenta­[c]­quinolin-4-ones is disclosed. Through C–C/N–O bond cleavage and C–H functionalization, the process enables one-carbon incorporation using cyclobutanone oximes to achieve [2 + 2 + 1] carboannulation of 1,7-enynes, which is highlighted by allowing the formation of four new bonds with high selectivity and broad substrate scope.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03643