Asymmetric syntheses of fused bicyclic compounds by conjugate additions of allylic organolithium species to activated olefins and subsequent cyclizations

S H Lim; M D Curtis; P Beak

doi:10.1021/ol007012+

Asymmetric syntheses of fused bicyclic compounds by conjugate additions of allylic organolithium species to activated olefins and subsequent cyclizations

Org Lett. 2001 Mar 8;3(5):711-4. doi: 10.1021/ol007012+.

Authors

S H Lim¹, M D Curtis, P Beak

Affiliation

¹ Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA.

PMID: 11259043
DOI: 10.1021/ol007012+

Abstract

[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.

Publication types

Research Support, U.S. Gov't, P.H.S.

MeSH terms

Alkenes / chemistry*
Bridged Bicyclo Compounds / chemical synthesis*
Crystallography, X-Ray
Cyclization
Ligands
Lithium Compounds / chemistry*
Magnetic Resonance Spectroscopy
Stereoisomerism

Substances

Alkenes
Bridged Bicyclo Compounds
Ligands
Lithium Compounds

Grants and funding

GM-18874/GM/NIGMS NIH HHS/United States