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Copper(i)/DM-SEGPHOS-catalyzed enantio- and diastereoselective conjugate boration to alpha-alkylidene-gamma-lactams
- Authors
- George, Jimit; Kim, Hun Young; Oh, Kyungsoo
- Issue Date
- 21-Feb-2020
- Publisher
- ROYAL SOC CHEMISTRY
- Citation
- ORGANIC CHEMISTRY FRONTIERS, v.7, no.4, pp 709 - 714
- Pages
- 6
- Journal Title
- ORGANIC CHEMISTRY FRONTIERS
- Volume
- 7
- Number
- 4
- Start Page
- 709
- End Page
- 714
- ISSN
- 2052-4129
2052-4129
- 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 alpha-alkylidene-gamma-lactams. The key structural feature of conjugate acceptors, alpha-alkylidene-gamma-lactams, was identified as the carbamate group such as N-Boc and N-Cbz, where the typical low reactivity and stereoselectivity issues associated with alpha,beta-unsaturated lactams as conjugate acceptors were resolved.
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