Diastereoselective synthesis of vicinal tertiary and N -substituted quaternary stereogenic centers by catalytic hydroalkylation of dienes

Chemical Science
Matthew J Goldfogel, Simon J Meek

Abstract

An efficient and diastereoselective (CDC)-Rh-catalyzed hydroalkylation of dienes with 1,3-oxazol-5(4H)-ones is reported. Aryl and alkyl substituted dienes are converted to α,α-substituted oxazolones (24 examples) by the formation of N-substituted quaternary carbon stereogenic centers in good yields (up to 96%) and with high diastereoselectivity (>20 : 1 dr). The reaction is tolerant of a range of dienes and oxazolones bearing various functional groups. Utility of the oxazolone products is illustrated through hydrolysis to form α,β-substituted α-amino acid analogues and stereoselective epoxidation of the resultant alkene to create four contiguous stereocenters.

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Citations

Sep 22, 2018·Angewandte Chemie·Siu-Chung ChanJason England
May 21, 2020·Advanced Synthesis & Catalysis·C Rose KennedyPaul J Chirik
Feb 15, 2018·Angewandte Chemie·Raphael DadaRylan J Lundgren
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Jan 8, 2021·Angewandte Chemie·Ryan T DavisonVy M Dong
Feb 28, 2017·Inorganic Chemistry·Lennart T Scharf, Viktoria H Gessner
Feb 27, 2020·Inorganic Chemistry·Siu-Chung ChanJason England

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