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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Mechanism and Stereoselectivity of the Phosphinylation of 3-Acyl Coumarins-Stereocontrol Via Concurrent Aromatic Interaction/Oxaphosphole Formation

Author(s): Petar Y. Petrov, Nikolay G. Vassilev, Silvia E. Angelova, Boris L. Shivachev and Galin P. Petrov

Volume 6, Issue 2, 2009

Page: [180 - 185] Pages: 6

DOI: 10.2174/157017809787582825

Price: $65

Abstract

Racemic P-acetoxy-P-chloro phenylphosphonite reacts with prochiral 3-acylcoumarins yielding (2R,3R)/(2S,3S)-coumarino-3,4-c-2-oxo-2-phenyl-1,2-3H-oxaphospholes with > 99% regio- and diastereoselectivity. The stereoselectivity is governed by the presence of phophonite phenyl group and oxaphosphole ring formation. The product has suitable conformation providing stereoselective route to (R,S)/(S,R) phosphino-substituted coumarins, normally inaccessible by the Phospha-Michael reaction employing achiral reagents.

Keywords: Phosphonylation, phosphinylation, diastereoselectivity, dynamic NMR, kinetics, oxaphospholes

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