TY - JOUR
T1 - Chiral relay in NHC-mediated asymmetric beta-lactam synthesis I; substituent effects in NHCs derived from (1R,2R)-cyclohexane-1,2-diamine
AU - Duguet, Nicolas
AU - Donaldson, Adele
AU - Leckie, Stuart M.
AU - Douglas, James
AU - Shapland, Peter
AU - Brown, Thomas B.
AU - Churchill, Gwydion
AU - Slawin, Alexandra M. Z.
AU - Smith, Andrew D.
PY - 2010/3/30
Y1 - 2010/3/30
N2 - The synthesis of a range of C-2-symmetric imidazolinium salts from (1R,2R)-cyclohexane-1,2-diamine, and an evaluation of the reactivity and asymmetric induction of the derived NHCs as catalysts for the asymmetric synthesis of beta-lactams, is reported. In this series, optimal enantioselectivity (up to 70% ee) is observed using N-benzyl or N-1-naphthylmethyl-substituted NHCs, consistent with a chiral relay effect operating to dictate the stereochemical outcome of this reaction. (C) 2010 Elsevier Ltd. All rights reserved.
AB - The synthesis of a range of C-2-symmetric imidazolinium salts from (1R,2R)-cyclohexane-1,2-diamine, and an evaluation of the reactivity and asymmetric induction of the derived NHCs as catalysts for the asymmetric synthesis of beta-lactams, is reported. In this series, optimal enantioselectivity (up to 70% ee) is observed using N-benzyl or N-1-naphthylmethyl-substituted NHCs, consistent with a chiral relay effect operating to dictate the stereochemical outcome of this reaction. (C) 2010 Elsevier Ltd. All rights reserved.
KW - N-HETEROCYCLIC CARBENE
KW - DIELS-ALDER REACTIONS
KW - INTRAMOLECULAR STETTER REACTION
KW - HIGHLY ENANTIOSELECTIVE SYNTHESIS
KW - CATALYZED RING EXPANSION
KW - C-CARBOXYL TRANSFER
KW - ALPHA-AMINO-ACIDS
KW - ALPHA,BETA-UNSATURATED ALDEHYDES
KW - KINETIC RESOLUTION
KW - LEWIS-ACID
UR - https://www.scopus.com/pages/publications/77953132255
U2 - 10.1016/j.tetasy.2010.03.001
DO - 10.1016/j.tetasy.2010.03.001
M3 - Article
SN - 0957-4166
VL - 21
SP - 582
EP - 600
JO - Tetrahedron: Asymmetry
JF - Tetrahedron: Asymmetry
IS - 5
ER -