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Practical Synthesis of Chiral Allylboronates by Asymmetric 1,1-Difunctionalization of Terminal Alkenes.
- Source :
-
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2022 Sep 12; Vol. 61 (37), pp. e202209076. Date of Electronic Publication: 2022 Aug 03. - Publication Year :
- 2022
-
Abstract
- We report herein a modular catalytic method for the efficient enantioselective synthesis of chiral allylboronates from abundant feedstock chemicals through an asymmetric 1,1-difunctionalization of alkenes. This protocol is distinguished by its use of an inexpensive chiral catalyst, mild and convenient reaction conditions, wide substrate scope, scalability and practicality. The utility of this method is demonstrated by the rapid synthesis of key intermediates of complex drug molecules. Mechanistic studies reveal that β-H elimination is a highly regioselective step and the reversible homolysis and convergance to the lower energy pre-reductive elimination intermediate is the enantio-determining step.<br /> (© 2022 Wiley-VCH GmbH.)
- Subjects :
- Catalysis
Cyclization
Molecular Structure
Stereoisomerism
Alkenes chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1521-3773
- Volume :
- 61
- Issue :
- 37
- Database :
- MEDLINE
- Journal :
- Angewandte Chemie (International ed. in English)
- Publication Type :
- Academic Journal
- Accession number :
- 35861349
- Full Text :
- https://doi.org/10.1002/anie.202209076