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- Title
Enantioselective Palladium‐Catalyzed [3+2] Cycloaddition of Trimethylenemethane and Fluorinated Ketones.
- Authors
Trost, Barry M.; Mata, Guillaume
- Abstract
Abstract: A nitrile‐substituted trimethylenemethane (TMM) donor undergoes palladium‐catalyzed [3+2] cycloadditions with fluorinated ketones to generate tetrasubstituted trifluoromethylated centers in high enantioselectivity under mild conditions. The generation of the palladium–TMM complex was achieved by a self‐deprotonation strategy, which shows remarkable improvements in regiocontrol, efficiency, and atom economy of asymmetric [3+2] cycloadditions. Moreover, the versatility of the nitrile group provides direct access to a variety of synthetically useful intermediates, including amides, aldehydes, and esters. The developed reaction conditions allow for the synthesis of a wide variety of aromatic, heteroaromatic, and aliphatic fluorinated dihydrofurans in excellent regio‐ and enantioselectivities.
- Subjects
TRIMETHYLENEMETHANE; PALLADIUM; AMIDES; ALDEHYDES; DIHYDROFURANS
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 38, p12513
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201807308