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Issue 14, 2019
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P-Chiral 1,7-diphosphanorbornenes: from asymmetric phospha-Diels–Alder reactions towards applications in asymmetric catalysis

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Abstract

A straightforward synthesis of P-chiral polycyclic phosphines by an asymmetric Diels–Alder reaction of 1-alkyl-1,2-diphospholes and (5R)-(L-menthyloxy)-2(5H)-furanone (MOxF) is presented. The [4 + 2] cycloaddition reaction of 1,2-diphospholes 1–3 with MOxF (4) proceeded with high diastereoselectivity (de up to 90%) resulting in the corresponding enantiopure anti-endo-1,7-diphosphanorbornenes 5a–7a. The absolute configuration of 5–7 was proved by a variety of 1D/2D NMR correlation methods. The use of the anti-endo-1,7-diphosphanorbornene 5a in the Pd-catalyzed asymmetric allylic alkylation of cinnamyl acetate 8 with cyclic β-ketoesters 9a,b provided up to 52% ee.

Graphical abstract: P-Chiral 1,7-diphosphanorbornenes: from asymmetric phospha-Diels–Alder reactions towards applications in asymmetric catalysis

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Article information


Submitted
30 Jan 2019
Accepted
12 Mar 2019
First published
13 Mar 2019

Dalton Trans., 2019,48, 4677-4684
Article type
Paper

P-Chiral 1,7-diphosphanorbornenes: from asymmetric phospha-Diels–Alder reactions towards applications in asymmetric catalysis

A. A. Zagidullin, E. S. Oshchepkova, I. V. Chuchelkin, S. A. Kondrashova, V. A. Miluykov, Sh. K. Latypov, K. N. Gavrilov and E. Hey-Hawkins, Dalton Trans., 2019, 48, 4677
DOI: 10.1039/C9DT00443B

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