Preparation of optically active six-membered P-heterocycles

A 3-phosphabicyclo[3.1.0] hexane 3-oxide, a 1,2-dihydrophosphinine 1-oxide, and a 1,2,3,6-tetrahydrophosphinine 1-oxide

Péter Bagi, Andrea Laki, G. Keglevich

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11 Citations (Scopus)

Abstract

The earlier described a 3-methyl-1-phenyl-3-phospholene 1-oxide (1) → 6,6-dichloro-1-methyl-3-phenyl-3-phosphabicyclo[3.1.0]hexane 3-oxide (2) → 4-chloro-1-phenyl-1,2-dihydrophosphinine 1-oxide (3) → 4-chloro-5-methyl-1- phenyl-1,2,3,6-tetrahydrophosphinine 1-oxide (4) reaction sequence was investigated from the point of view of preparing optically active intermediates/products (2-4). In principle, both the resolution of the corresponding racemic products and the transformation of the optically active starting materials are suitable approaches for the preparation of optically active six-membered P-heterocycles (2-4). Racemization occurred during the dichlorocyclopropanation reaction of (S)-3-methyl-1-phenyl-3-phospholene 1-oxide ((S)-1), but the thermolytic ring opening of (-)-2, and the selective reduction of α,β-double bond of (-)-3 did not cause the loss of optical activity. First in the literature, the resolution of a 3-phosphabicyclo[3.1.0] hexane 3-oxide (2) and a 1,2,3,6-tetrahydrophosphinine 1-oxide (4) was elaborated.

Original languageEnglish
Pages (from-to)179-186
Number of pages8
JournalHeteroatom Chemistry
Volume24
Issue number3
DOIs
Publication statusPublished - May 2013

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Hexanes
Oxides

ASJC Scopus subject areas

  • Chemistry(all)

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title = "Preparation of optically active six-membered P-heterocycles: A 3-phosphabicyclo[3.1.0] hexane 3-oxide, a 1,2-dihydrophosphinine 1-oxide, and a 1,2,3,6-tetrahydrophosphinine 1-oxide",
abstract = "The earlier described a 3-methyl-1-phenyl-3-phospholene 1-oxide (1) → 6,6-dichloro-1-methyl-3-phenyl-3-phosphabicyclo[3.1.0]hexane 3-oxide (2) → 4-chloro-1-phenyl-1,2-dihydrophosphinine 1-oxide (3) → 4-chloro-5-methyl-1- phenyl-1,2,3,6-tetrahydrophosphinine 1-oxide (4) reaction sequence was investigated from the point of view of preparing optically active intermediates/products (2-4). In principle, both the resolution of the corresponding racemic products and the transformation of the optically active starting materials are suitable approaches for the preparation of optically active six-membered P-heterocycles (2-4). Racemization occurred during the dichlorocyclopropanation reaction of (S)-3-methyl-1-phenyl-3-phospholene 1-oxide ((S)-1), but the thermolytic ring opening of (-)-2, and the selective reduction of α,β-double bond of (-)-3 did not cause the loss of optical activity. First in the literature, the resolution of a 3-phosphabicyclo[3.1.0] hexane 3-oxide (2) and a 1,2,3,6-tetrahydrophosphinine 1-oxide (4) was elaborated.",
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AB - The earlier described a 3-methyl-1-phenyl-3-phospholene 1-oxide (1) → 6,6-dichloro-1-methyl-3-phenyl-3-phosphabicyclo[3.1.0]hexane 3-oxide (2) → 4-chloro-1-phenyl-1,2-dihydrophosphinine 1-oxide (3) → 4-chloro-5-methyl-1- phenyl-1,2,3,6-tetrahydrophosphinine 1-oxide (4) reaction sequence was investigated from the point of view of preparing optically active intermediates/products (2-4). In principle, both the resolution of the corresponding racemic products and the transformation of the optically active starting materials are suitable approaches for the preparation of optically active six-membered P-heterocycles (2-4). Racemization occurred during the dichlorocyclopropanation reaction of (S)-3-methyl-1-phenyl-3-phospholene 1-oxide ((S)-1), but the thermolytic ring opening of (-)-2, and the selective reduction of α,β-double bond of (-)-3 did not cause the loss of optical activity. First in the literature, the resolution of a 3-phosphabicyclo[3.1.0] hexane 3-oxide (2) and a 1,2,3,6-tetrahydrophosphinine 1-oxide (4) was elaborated.

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