Diastereo- and Enantioselective CuH-Catalyzed Hydroamination of Strained Trisubstituted Alkenes
Name
Diastereo-_and_Enantioselective_CuH-Catalyzed_Hydroamination_of_Strained_Trisubstituted_Alkenes_v1.pdf
Description
Submitted version
Size
9.34 MB
Format
Adobe PDF
Checksum (MD5)
29e3ff386b48b1c1fe57cb28ad99ee59
Author(s)
Feng, Sheng
Hao, Hua
Liu, Peng
Buchwald, Stephen Leffler
Date Issued
November 2019
Journal
ACS Catalysis
Publisher
American Chemical Society (ACS)
Citation
Feng, Sheng et al. "Diastereo- and Enantioselective CuH-Catalyzed Hydroamination of Strained Trisubstituted Alkenes." ACS Catalysis 10, 1 (November 2019): 282-291 © 2019 American Chemical Society
Version
Original manuscript
Abstract
Amine-substituted cyclobutanes and cyclopropanes are important substructures in biologically active compounds. Moreover, many of the cycloalkane units bear multiple substituents and stereocenters. Therefore, synthetic methods that produce polysubstituted aminocyclobutanes and aminocyclopropanes in a highly diastereo- and enantioselective manner are of importance. Herein, we describe the diastereo- and enantioselective synthesis of various types of polysubstituted aminocyclobutanes and aminocyclopropanes through CuH-catalyzed hydroamination of 1-substituted cyclobutenes and cyclopropenes. These strained trisubstituted alkenes exhibit much higher reactivity compared to their unstrained analogues in the initial hydrocupration step of the reaction. Moreover, an interesting reversal of regioselectivity was observed in the hydroamination of 1-aryl-substituted cyclobutenes compared to the cyclopropene analogues. The origins of the enhanced reactivity of strained trisubstituted alkenes as well as the differences in the regio- and enantioselectivity between reactions with cyclobutenes and cyclopropenes were investigated computationally.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/acscatal.9b04871
