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Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes

Author(s)
Bayeh-Romero, Liela; Buchwald, Stephen Leffler
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Abstract
The general enantioselective synthesis of axially chiral disubstituted allenes from prochiral starting materials remains a long-standing challenge in organic synthesis. Here, we report an efficient enantio- and chemoselective copper hydride catalyzed semireduction of conjugated enynes to furnish 1,3-disubstituted allenes using water as the proton source. This protocol is sufficiently mild to accommodate an assortment of functional groups including keto, ester, amino, halo, and hydroxyl groups. Additionally, applications of this method for the selective synthesis of monodeuterated allenes and chiral 2,5-dihydropyrroles are described.
Date issued
2019-08
URI
https://hdl.handle.net/1721.1/122287
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Bayeh-Romero, Liela and Stephen L. Buchwald. "Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes." Journal of the American Chemical Society 141, 35 (August 2019): 13788-13794 © 2019 American Chemical Society
Version: Final published version
ISSN
0002-7863
1520-5126

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