Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 23, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202117696
Keywords
Asymmetric Catalysis; Carboboration; Copper; gem-Dichlorides; Skipped Dienes
Categories
Funding
- AEI [PID2020-118237RB-I00]
- Xunta de Galicia [ED431C 2018/04, ED431G 2019/03]
- European Union (European Regional Development Fund - ERDF)
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Allylic gem-dichlorides can be efficient substrates for catalytic asymmetric allylboration of alkynes. The method generates chiral skipped dienes with excellent levels of chemo-, regio- enantio- and diastereoselectivity, making them versatile building blocks for the synthesis of optically active compounds.
Allylic gem-dichlorides are shown to be efficient substrates for catalytic asymmetric allylboration of alkynes. The method employs a chiral NHC-Cu catalyst capable of generating in a single step chiral skipped dienes bearing a Z-alkenyl chloride, a trisubstituted E-alkenyl boronate and a bis-allylic stereocenter with excellent levels of chemo-, regio- enantio- and diastereoselectivity. This high degree of functionalization makes these products versatile building blocks as illustrated with the synthesis of several optically active compounds. DFT calculations support the key presence of a metal cation bridge ligand-substrate interaction and account for the stereoselectivity outcome.
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