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Controlling the Course of Nucleophilic Additions to ortho ‐Substituted (η 6 ‐Anisole)tricarbonyl‐chromium Complexes: Dienol Ether Formation versus tele ‐Substitution
Author(s) -
Schmalz HansGünther,
Schellhaas Kurt
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199621461
Subject(s) - anisole , nucleophilic substitution , ether , chemistry , reagent , medicinal chemistry , chromium , substitution reaction , nucleophile , organic chemistry , catalysis
Chlorotrimethylsilane is the reagent of choice to trap the ionic intermediate that arises on nucleophilic addition to ortho ‐substituted anisoletricarbonylchromium complexes and to suppress its tendency toward tele ‐substitution (relative to the methoxy group). Thus the planar‐chiral complex 1 can be transformed into the cyclo‐hexenone 2 with complete retention of the stereochemical information in greater than 95% ee . Compound 2 is a promising precursor for the total synthesis of (+)‐ptilocaulin.