Asymmetric syntheses of fused bicyclic compounds by conjugate additions of allylic organolithium species to activated olefins and subsequent cyclizations.
[reaction: see text]. Addition of the configurationally stable organolithium species produced by enantioselective deprotonation of N-Boc-N-(p-methoxyphenyl) allylamines to alpha,beta-unsaturated carbonyl compounds affords 1,4-addition products in good yields with high diastereomeric and enantiomeric ratios. Further transformations of these compounds provide [3.3.0]-, [4.3.0]-, [5.3.0]-, and [5.4.0]-carbocycles and heterocycles with high stereoselectivities.
Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA.
S H
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Lim
M D
MD
Curtis
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P
Beak
D000475:Alkenes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D003500:Cyclization; D008024:Ligands; D018020:Lithium Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
D000475:Alkenes; D001643:Bridged Bicyclo Compounds; D008024:Ligands; D018020:Lithium Compounds