A C–H bond activation-based catalytic approach to tetrasubstituted chiral allenes

Shangze Wu, Xin Huang, Wangteng Wu, Pengbin Li, Chunling Fu and Shengming Ma ()
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Shangze Wu: Laboratory of Molecular Recognition and Synthesis, Zhejiang University
Xin Huang: Laboratory of Molecular Recognition and Synthesis, Zhejiang University
Wangteng Wu: Laboratory of Molecular Recognition and Synthesis, Zhejiang University
Pengbin Li: Laboratory of Molecular Recognition and Synthesis, Zhejiang University
Chunling Fu: Laboratory of Molecular Recognition and Synthesis, Zhejiang University
Shengming Ma: Laboratory of Molecular Recognition and Synthesis, Zhejiang University

Nature Communications, 2015, vol. 6, issue 1, 1-9

Abstract: Abstract Enantioselective synthesis of fully substituted allenes has been a challenge due to the non-rigid nature of the axial chirality, which spreads over three carbon atoms. Here we show the commercially available simple Rh complex may catalyse the CMD (concerted metalation/deprotonation)-based reaction of the readily available arenes with sterically congested tertiary propargylic carbonates at ambient temperature affording fully substituted allenes. It is confirmed that the excellent designed regioselectivity for the C–C triple bond insertion is induced by the coordination of the carbonyl group in the directing carbonate group as well as the steric effect of the tertiary O-linked carbon atom. When an optically active carbonate was used, surprisingly high efficiency of chirality transfer was realized, affording fully substituted allenes in excellent enantiomeric excess (ee).

Date: 2015
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DOI: 10.1038/ncomms8946

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