Solid-State Photochemical Reaction of S-Phenyl-N-(benzoylformyl)thiocarbamates: "Absolute" Asymmetric Synthesis Using the Chiral Crystal Environment
β Scribed by Sakamoto, Masami; Takahashi, Masaki; Fujita, Tsutomu; Nishio, Takehiko; Iida, Ikuo; Watanabe, Shoji
- Book ID
- 126888283
- Publisher
- American Chemical Society
- Year
- 1995
- Tongue
- English
- Weight
- 276 KB
- Volume
- 60
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
Solid State Photochemical Reaction of Achiral N-(Ξ²,Ξ³-Unsaturated Carbonyl)thiocarbamate to Optically Active Thiolactone in the Chiral Crystalline Environment. -The solid-state photoreaction, leading to optically active Ξ³-thiolactone (II), proceeds via intramolecular [2 + 2] thietane formation and s
Due to the matrix effect of the crystal lattice, irradiation of alcohol 2 could be produced, depending on which enantiomorphic form of the chiral crystal was irradiated. As ketone 1 yields 2 diastereoselectively as the main product (97% de). Furthermore, the chiral crystal environment in the ketone