Enantioselective Nickel-Catalyzed anti-Carbometallative Cyclizations of Alkynyl Electrophiles Enabled by Reversible Alkenylnickel E/Z Isomerization | Zendy

Christopher J. Clarke | Zendy; Celia A. IncertiPradillos | Zendy; Hon Wai Lam | Zendy

Open Access

Enantioselective Nickel-Catalyzed anti-Carbometallative Cyclizations of Alkynyl Electrophiles Enabled by Reversible Alkenylnickel E/Z Isomerization

Author(s) -

Christopher J. Clarke,

Celia A. IncertiPradillos,

Hon Wai Lam

Publication year - 2016

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.6b04206

Subject(s) - chemistry , isomerization , enantioselective synthesis , electrophile , catalysis , alkyne , nickel , medicinal chemistry , stereochemistry , organic chemistry

Nickel-catalyzed additions of arylboronic acids to alkynes, followed by enantioselective cyclizations of the alkenylnickel species onto tethered ketones or enones, are reported. These reactions are reliant upon the formal anti-carbonickelation of the alkyne, which is postulated to occur by the reversible E/Z isomerization of an alkenylnickel species.

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