Nickel-Catalyzed Vinylidene Insertions into O–H Bonds | Zendy

Houng Kang | Zendy; Christopher Uyeda | Zendy

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Nickel-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.

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