Open AccessNickel-Catalyzed Vinylidene Insertions into O–H Bonds
Author(s) -
Houng Kang,
Christopher Uyeda
Publication year - 2020
Publication title -
acs catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 4.898
H-Index - 198
ISSN - 2155-5435
DOI - 10.1021/acscatal.0c04713
Subject(s) - catalysis , oxazoline , nickel , reductive elimination , chemistry , pyridine , combinatorial chemistry , aldol reaction , enantioselective synthesis , stereochemistry , medicinal chemistry , organic chemistry
A (pybox)Ni catalyst (pybox = pyridine-bis(oxazoline)) promotes the reductive cyclization of β-hydroxy 1,1-dichloroalkenes to form 2,3-dihydrofurans. The substrates for this reaction are conveniently prepared by an aldol addition followed by one-carbon homologation. Chiral substrates are accessible in highly enantioenriched form, allowing for the synthesis of stereochemically complex 2,3,4-trisubstituted products. Mechanistic studies support a vinylidene O-H insertion pathway rather than C-O cross-coupling followed by reductive dechlorination.