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Dynamic kinetic asymmetric arylation and alkenylation of ketones.
- Source :
-
Science . 2/17/2023, Vol. 379 Issue 6633, p662-670. 9p. 6 Color Photographs. - Publication Year :
- 2023
-
Abstract
- Despite the importance of enantioenriched alcohols in medicinal chemistry, total synthesis, and materials science, the efficient and selective construction of enantioenriched tertiary alcohols bearing two contiguous stereocenters has remained a substantial challenge. We report a platform for their preparation through the enantioconvergent, nickel-catalyzed addition of organoboronates to racemic, nonactivated ketones. We prepared several important classes of a,b-chiral tertiary alcohols in a single step with high levels of diastereo- and enantioselectivity through a dynamic kinetic asymmetric addition of aryl and alkenyl nucleophiles. We applied this protocol to modify several profen drugs and to rapidly synthesize biologically relevant molecules. We expect this nickel-catalyzed, base-free ketone racemization process to be a widely applicable strategy for the development of dynamic kinetic processes. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ARYLATION
*PHARMACEUTICAL chemistry
*ALKENYLATION
*KETONES
*NUCLEOPHILES
Subjects
Details
- Language :
- English
- ISSN :
- 00368075
- Volume :
- 379
- Issue :
- 6633
- Database :
- Academic Search Index
- Journal :
- Science
- Publication Type :
- Academic Journal
- Accession number :
- 161950010
- Full Text :
- https://doi.org/10.1126/science.ade0760