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The synthesis of optically active P-heterocycles

✍ Scribed by György Keglevich; Judit Dvorszki; Viktória Ujj; Krisztina Ludányi

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
128 KB
Volume
21
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

Optically active 1‐alkoxy‐ and 1‐amino‐3‐phospholene oxides were synthesized by the reaction of the corresponding 1‐chloro‐3‐phospholene oxides with (1__R__,2__S__,5__R__)‐(–)menthol and (S)‐(–)‐α‐phenylethylamine. The 3‐methyl‐3‐phospholene oxides were subjected to dichlorocyclopropanation under liquid–liquid phase transfer catalytic conditions to afford the 3‐phosphabicyclo[3.1.0]hexane 3‐oxides as a mixture of four diastereomers. Thermolysis of the menthyl‐phosphabicyclohexane oxides led to the corresponding 1,2‐dihydrophosphinine oxide as a diastereomeric mixture of two double‐bond isomers. As a result of additional steps, the dichlorocarbene addition reaction of the 1‐menthyl‐3,4‐dimethyl‐3‐phospholene oxide resulted in eventually, the formation of a 4‐dichloromethylene‐1,4‐dihydrophosphinine oxide. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:271–277, 2010; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20599

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