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Published on: February 27, 2017
Nickel Catalyzed Vinylidene Insertions into O-H Bonds
Houng Kang1, Christopher Uyeda1
1Department of Chemistry, Purdue University, West Lafayette, IN 47907, United States.
Abstract:
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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