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

preprint
submitted on 23.07.2019, 18:32 and posted on 24.07.2019, 12:12 by Liela Bayeh, Stephen L. Buchwald
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 semi-reduction 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 mono-deuterated allenes and chiral 2,5-dihydropyrroles are described.

Funding

The Arnold and Mabel Beckman Foundation

R35-GM122483

History

Email Address of Submitting Author

lbayeh@mit.edu

Institution

Massachusetts Institute of Technology (MIT)

Country

United States

ORCID For Submitting Author

0000-0001-5532-756X

Declaration of Conflict of Interest

No Conflict of Interest

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