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

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초록

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.

키워드

ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS; ENANTIOSELECTIVE BETA-BORATION; CATALYTIC ASYMMETRIC-SYNTHESIS; ESTERS; ADDITIONS; HYDROGENATION; HYDROBORATION; BORYLATION; TERTIARY; BOND
제목
Copper(i)/DM-SEGPHOS-catalyzed enantio- and diastereoselective conjugate boration to α-alkylidene-γ-lactams
저자
George, Jimit; Kim, Hun Young; Oh, Kyungsoo
DOI
10.1039/c9qo01504c
발행일
2020-02
유형
Article
저널명
Organic Chemistry Frontiers
권
7
호
4
페이지
709 ~ 714