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Issue 20, 2020
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Regio- and diastereoselective reactions of chiral secondary alkylcopper reagents with propargylic phosphates: preparation of chiral allenes

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Abstract

The diastereoselective SN2′-substitution of secondary alkylcopper reagents with propargylic phosphates enables the preparation of stereodefined alkylallenes. By using enantiomerically enriched alkylcopper reagents and enantioenriched propargylic phosphates as electrophiles anti-SN2′-substitutions were performend leading to α-chiral allenes in good yields with excellent regioselectivity and retention of configuration. DFT-calculations were performed to rationalize the structure of these alkylcopper reagents in various solvents, emphasizing their configurational stability in THF.

Graphical abstract: Regio- and diastereoselective reactions of chiral secondary alkylcopper reagents with propargylic phosphates: preparation of chiral allenes

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Supplementary files

Article information


Submitted
26 Nov 2019
Accepted
07 Apr 2020
First published
14 May 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 5328-5332
Article type
Edge Article

Regio- and diastereoselective reactions of chiral secondary alkylcopper reagents with propargylic phosphates: preparation of chiral allenes

J. Skotnitzki, A. Kremsmair, D. Keefer, F. Schüppel, B. Le Cacher de Bonneville, R. de Vivie-Riedle and P. Knochel, Chem. Sci., 2020, 11, 5328
DOI: 10.1039/C9SC05982B

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