Highly selective photoreactions of α-oxoamides and α-tropolone alkyl ethers in crystalline inclusion complexes
✍ Scribed by Fumio Toda; Koichi Tanaka; Minoru Yagi
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 716 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
Control of photocyclization of three a-oxoamides in crystalline inclusion complexes with three kinds of host compounds was studied. In all cases, S-lactams were obtained exclusively.
In two cases, cis-8-lactams were formed selectively. By an enantioselective control using an optically active host compound, 1,6-di(o-chlorophenyl)-1,6-diphenylhexa-2,4-diyne-1,6-diol, optically active 8-lactams of high enantiomerit excess were obtained.
Irradiation of complexes of atropolone alkyl ethers with the above optically active host compound in a solid state, oave the [2+21 photoreaction product, l-aikoxybicyclo[3.2.O]heptal3,6-dien-2-one; and its ringlopened derivative, alkyl 4-oxo-2-cyclopentene-l-acetate, in 100 and 72-91% enantiomeric excess, respectively.