☆ 4.8 Article

Controllable O-Nucleometalation Cyclization Strategy: Access to Divergent Ring-Functionalized Molecules

ORGANIC LETTERS (2016)

Journal

ORGANIC LETTERS

Volume 18, Issue 24, Pages 6232-6235

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/acs.orglett.6b02710

Keywords

-

Categories

Chemistry, Organic

Funding

National Key Research and Development Program of China [2016YFA0602900]
National Natural Science Foundation of China [21472051, 21420102003, 21490572]
Pearl River S&T Nova Program of Guangzhou [201610010160]

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Abstract

The vinyl moiety-assisted selective O-nucleopalladation is reported, which offers rapid constructions of cycloolefins and cyclopropanes via oxidant-induced cyclization of enynes. O-2 resulted in the unexpected 6-endo-Heck cyclization, while CuCl2 led to a 5-exo-trig pathway and synergetic S(N)2-type C-C bond formation. Amide works as an O-transferred nucleophilic group to activate the alkyne moiety, which induced divergent annulation processes. Moreover, the regenerated amides could be used for further modifications.

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