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Enantioselective One‐Pot Conjugate Addition of Grignard Reagents Followed by a Mannich Reaction
Author(s) -
Šebesta Radovan,
Bilčík Filip,
Fodran Peter
Publication year - 2010
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/ejoc.201000773
Subject(s) - chemistry , enantioselective synthesis , stereocenter , diastereomer , conjugate , reagent , ferrocene , mannich reaction , grignard reaction , organic chemistry , grignard reagent , cyclohexenone , addition reaction , catalysis , mathematical analysis , mathematics , electrode , electrochemistry
Asymmetric addition of Grignard reagents to cyclohexenone, catalyzed by ferrocene diphosphanes, afforded chiral magnesium enolates. These enolates reacted in a one‐pot arrangement with N ‐benzylidenetoluenesulfonamide to give β‐amino carbonyl compounds with three contiguous stereocenters. Two major diastereoisomers ( dr = 60:40) of product with enantioselectivities up to 95 % ee were separated by flash chromatography.