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Enantioselective and site-specific copper-catalyzed reductive allyl–allyl cross-coupling of allenes

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Abstract

A copper-catalyzed asymmetric reductive allyl–allyl cross-coupling reaction of allenes with allylic phosphates wherein allenes were used as allylmetal surrogates has been achieved for the first time. This protocol provides an efficient and straightforward route to optically active 1,5-dienes in a highly enantioselective and site-specific fashion. Furthermore, all-carbon quaternary stereogenic centers could also be constructed with this protocol. The versatility of the products is demonstrated through a diverse array of further transformations of the enantioenriched 1,5-dienes.

Graphical abstract: Enantioselective and site-specific copper-catalyzed reductive allyl–allyl cross-coupling of allenes

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Publication details

The article was received on 10 Oct 2018, accepted on 03 Dec 2018 and first published on 04 Dec 2018


Article type: Edge Article
DOI: 10.1039/C8SC04505D
Citation: Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
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    Enantioselective and site-specific copper-catalyzed reductive allyl–allyl cross-coupling of allenes

    G. Xu, B. Fu, H. Zhao, Y. Li, G. Zhang, Y. Wang, T. Xiong and Q. Zhang, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C8SC04505D

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