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Issue 4, 2020
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Copper(i)/DM-SEGPHOS-catalyzed enantio- and diastereoselective conjugate boration to α-alkylidene-γ-lactams

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Abstract

A combination of CuCl and DM-SEGPHOS catalyst system has allowed the development of highly enantioselective and diastereoselective conjugate addition of bis(pinacolato)diboron to α-alkylidene-γ-lactams. The key structural feature of conjugate acceptors, α-alkylidene-γ-lactams, was identified as the carbamate group such as N-Boc and N-Cbz, where the typical low reactivity and stereoselectivity issues associated with α,β-unsaturated lactams as conjugate acceptors were resolved.

Graphical abstract: Copper(i)/DM-SEGPHOS-catalyzed enantio- and diastereoselective conjugate boration to α-alkylidene-γ-lactams

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Supplementary files

Article information


Submitted
19 Dec 2019
Accepted
15 Jan 2020
First published
20 Jan 2020

Org. Chem. Front., 2020,7, 709-714
Article type
Research Article

Copper(I)/DM-SEGPHOS-catalyzed enantio- and diastereoselective conjugate boration to α-alkylidene-γ-lactams

J. George, H. Y. Kim and K. Oh, Org. Chem. Front., 2020, 7, 709
DOI: 10.1039/C9QO01504C

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