| Popis: |
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. © 2013 Wiley Periodicals, Inc. Heteroatom Chem 24:179–186, 2013; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.21080 |
