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- Title
Enantioselective Hydroalkenylation and Hydroalkynylation of Alkenes Enabled by a Transient Directing Group: Catalyst Generality through Rigidification**.
- Authors
Simlandy, Amit Kumar; Alturaifi, Turki M.; Nguyen, Johny M.; Oxtoby, Lucas J.; Wong, Quynh Nguyen; Chen, Jason S.; Liu, Peng; Engle, Keary M.
- Abstract
The catalytic enantioselective synthesis of α‐chiral alkenes and alkynes represents a powerful strategy for rapid generation of molecular complexity. Herein, we report a transient directing group (TDG) strategy to facilitate site‐selective palladium‐catalyzed reductive Heck‐type hydroalkenylation and hydroalkynylation of alkenylaldehyes using alkenyl and alkynyl bromides, respectively, allowing for construction of a stereocenter at the δ‐position with respect to the aldehyde. Computational studies reveal the dual beneficial roles of rigid TDGs, such as L‐tert‐leucine, in promoting TDG binding and inducing high levels of enantioselectivity in alkene insertion with a variety of migrating groups.
- Subjects
ALKENES; CATALYSTS; ALKYNES; PALLADIUM catalysts; ALDEHYDES; BROMIDES
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 29, p1
- ISSN
0044-8249
- Publication type
Academic Journal
- DOI
10.1002/ange.202304013