Diastereo- and Enantioselective δ-H Abstraction in the Solid State of 1-Benzoyl-8-benzylnaphthalene – Absolute Asymmetric Synthesis Due to a Chiral Crystal Environment
✍ Scribed by Hermann Irngartinger; Peter Walter Fettel; Volker Siemund
- Publisher
- John Wiley and Sons
- Year
- 1998
- Tongue
- English
- Weight
- 175 KB
- Volume
- 1998
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
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 1 is achiral and the chiral induction is caused exclusively by physical influences, this reaction represents a single crystals of 1 (space group P2 1 2 1 2 1 ) also renders the reaction enantioselective (86% ee). Both enantiomers of further example of an absolute asymmetric synthesis.