Synthesis of optically active 1-aza-4-oxabicyclo[4.1.0]-heptan-5-ones
β Scribed by O. N. Krutius; A. V. Eremeev; F. D. Polyak; G. V. Shustov; V. N. Voznesenskii; I. I. Chervin; R. G. Kostyanovskii
- Publisher
- Springer US
- Year
- 1989
- Tongue
- English
- Weight
- 377 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0009-3122
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## Abstract Dehydrochlorination of chlorinated 5βhydroxyβ2βoxabicyclo[3.2.0]heptanβ4βones, 3aβc, which were obtained from the photo[2+2]cycloadditions between 4βhydroxyβ3(2__H__)βfuranone 1 and chloroethylenes, with triethylamine gave 2βethenylβ3(2__H__)βfuranones 4a,b or 2β(2βcyanoethyl)β3(2__H__)
The racemic title bicycle (V) undergoes spontaneous resolution on crystallization from chloroform or acetone. The absolute configuration of the obtained enantiopure product (16-44% e.e.) is determined by comparison with (S)-(V) derived from (S)-Ser-OMe (I). Mutarotation due to partial conversion of