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

24 July 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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 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.

Keywords

Copper Hydride
copper hydride catalysis
Allene Synthesis
Asymmetric Catalysis

Supplementary materials

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Supporting Information
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NMR Spectra
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SFC GC and HPLC Traces
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