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Diastereo‐ and Enantioselective δ‐H Abstraction in the Solid State of 1‐Benzoyl‐8‐benzylnaphthalene – Absolute Asymmetric Synthesis Due to a Chiral Crystal Environment
Author(s) -
Irngartinger Hermann,
Walter Fettel Peter,
Siemund Volker
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199810)1998:10<2079::aid-ejoc2079>3.0.co;2-e
Subject(s) - enantioselective synthesis , chemistry , ketone , absolute configuration , enantiomer , crystal structure , alcohol , enantiomeric excess , stereochemistry , crystallography , organic chemistry , catalysis
Due to the matrix effect of the crystal lattice, irradiation of ketone 1 yields 2 diastereoselectively as the main product (97% de ). Furthermore, the chiral crystal environment in single crystals of 1 (space group P 2 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 ketone 1 is achiral and the chiral induction is caused exclusively by physical influences, this reaction represents a further example of an absolute asymmetric synthesis.