DIASTEREOSELECTIVE AND ENANTIOSELECTIVE DELTA-H ABSTRACTION IN THE SOLID-STATE OF 1-BENZOYL-8-BENZYLNAPHTHALENE - ABSOLUTE ASYMMETRIC-SYNTHESIS DUE TO A CHIRAL CRYSTAL ENVIRONMENT

Due to the matrix effect of the crystal lattice, irradiation of ketone 1 yields 2 diastereoselectively as the main product (97% de). Further more, the chiral crystal environment in single crystals of 1 (space gr oup P2(1)2(1)2(1)) also renders the reaction enantioselective (86% ee) . Both enantiomers of alcohol 2 could be produced, depending on which enantiomorphic form of the chiral crystal was irradiated. As the keton e 1 is achiral and the chiral induction is caused exclusively by physi cal influences, this reaction represents a further example of an absol ute asymmetric synthesis.