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Cobalt-Catalyzed Asymmetric Sequential Hydroboration/Isomerization/Hydroboration of 2-Aryl Vinylcyclopropanes.
- Source :
-
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2022 Jul 25; Vol. 61 (30), pp. e202205619. Date of Electronic Publication: 2022 Jun 10. - Publication Year :
- 2022
-
Abstract
- A cobalt-catalyzed asymmetric sequential hydroboration/isomerization/hydroboration of 2-aryl vinylcyclopropanes was for the first time reported for the preparation of valuable chiral 1,5-bis(boronates) in good yields with excellent enantioselectivity via asymmetric sequential isomerization/hydroboration of a trisubstituted alkene intermediate. The reaction was carried out smoothly and this protocol was used for asymmetric syntheses of (-)-preclamol in gram-scale. The two primary C <superscript>(sp3)</superscript> -B bonds in chiral 1,5-bis(boronates) could be distinguished in iterative Suzuki-Miyaura cross-coupling reaction, delivering chiral 1,2,5-triaryl alkanes with excellent enantioselectivity. Based on experimental and computational studies, a cobalt-hydride species was proposed as the active intermediate in hydroboration, isomerization, and second hydroboration reactions.<br /> (© 2022 Wiley-VCH GmbH.)
- Subjects :
- Catalysis
Isomerism
Stereoisomerism
Alkenes chemistry
Cobalt chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1521-3773
- Volume :
- 61
- Issue :
- 30
- Database :
- MEDLINE
- Journal :
- Angewandte Chemie (International ed. in English)
- Publication Type :
- Academic Journal
- Accession number :
- 35607762
- Full Text :
- https://doi.org/10.1002/anie.202205619