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Diastereodivergent and Enantioselective Synthesis of Homoallylic Alcohols via Nickel-Catalyzed Borylative Coupling of 1,3-Dienes with Aldehydes
- Source :
- Journal of the American Chemical Society; September 2023, Vol. 145 Issue: 35 p19195-19201, 7p
- Publication Year :
- 2023
-
Abstract
- We present the first enantioselective nickel-catalyzed borylative coupling of 1,3-dienes with aldehydes, providing an efficient route to highly valuable homoallylic alcohols in a single step. The reaction involves the 1,4-carboboration of dienes, leading to the formation of C–C and C–B bonds accompanied by the construction of two continuous stereogenic centers. Enabled by a chiral spiro phosphine-oxazoline nickel complex, this transformation yields products with exceptional diastereoselectivity, E-selectivity, and enantioselectivity. The diastereoselectivity of the reaction can be controlled by employing either (Z)-1,3-dienes or (E)-1,3-dienes.
Details
- Language :
- English
- ISSN :
- 00027863 and 15205126
- Volume :
- 145
- Issue :
- 35
- Database :
- Supplemental Index
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Periodical
- Accession number :
- ejs63812431
- Full Text :
- https://doi.org/10.1021/jacs.3c07697