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Stereoselective preparation of P,axial-stereogenic allenyl bisphosphine oxides via chirality-transfer

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Abstract

P,C-Stereogenic propargyl alcohols RC-3/SC-3′ were prepared by the addition of (L)-menthyl-derived SPOs to propynals, which were converted to P,axial-stereogenic allenyl bisphosphine oxides. The chirality transfer was controlled by α-carbon via syn [2,3]-sigmatropic rearrangement. For SC-3′ linking weak WDG on the alkynyl moiety, the chirality on the axis depended on stereogenic phosphorus.

Graphical abstract: Stereoselective preparation of P,axial-stereogenic allenyl bisphosphine oxides via chirality-transfer

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Article information


Submitted
07 Mar 2020
Accepted
24 Mar 2020
First published
25 Mar 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

Stereoselective preparation of P,axial-stereogenic allenyl bisphosphine oxides via chirality-transfer

M. Qiu, H. Zheng, J. Ye, B. Yan, C. Zhao and Q. Li, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00390E

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