Asymmetric Synthesis of α‑Alkylidene-β-Lactams through Copper Catalysis with a Prolinol-Phosphine Chiral Ligand

A copper/prolinol-phosphine chiral catalyst enabled the one-step synthesis of chiral α-alkylidene-β-lactams. Optimization of the chiral ligand for steric and electronic properties realized the highly enantioselective coupling of nitrones and propargyl alcohol derived alkynes. The resulting chiral α-...

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Bibliographic Details
Published in:Organic letters 2019-03, Vol.21 (6), p.1717-1721
Main Authors: Imai, Koji, Takayama, Yurie, Murayama, Hiroaki, Ohmiya, Hirohisa, Shimizu, Yohei, Sawamura, Masaya
Format: Article
Language:English
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Summary:A copper/prolinol-phosphine chiral catalyst enabled the one-step synthesis of chiral α-alkylidene-β-lactams. Optimization of the chiral ligand for steric and electronic properties realized the highly enantioselective coupling of nitrones and propargyl alcohol derived alkynes. The resulting chiral α-alkylidene-β-lactams served as a platform for various β-lactams via well-established transformations of α,β-unsaturated carbonyl compounds.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00276