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Asymmetric syn ‐Selective Michael Addition of Enolates to Chiral 8‐Phenylmenthyloxy Vinyl Chromium Carbene Complexes
Author(s) -
Barluenga José,
Montserrat Javier M.,
Flórez Josefa,
GarciaGranda Santiago,
Martin Eduardo
Publication year - 1995
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.19950010407
Subject(s) - stereocenter , aldol reaction , michael reaction , chemistry , adduct , reagent , enol , ketone , carbene , enantiomer , methyl vinyl ketone , asymmetric induction , lithium (medication) , addition reaction , chromium , medicinal chemistry , organic chemistry , enantioselective synthesis , catalysis , medicine , endocrinology
Michael addition reactions of ketone and ester lithium enolates to optically active Fischer vinylcarbene complexes derived from (‐)‐8‐phenylmenthol take place with high syn selectivity and high levels of asymmetric induction. The initial Michael adducts can be further elaborated through diastereoselective addition of organometallic reagents to ketones and aldol reactions. Removal of the metal fragment and chiral auxiliary group leads to cyclic enol ethers with three or five contiguous stereogenic centers and of high enantiomeric purity.