Enantioselective synthesis of bridged bicyclic ring systems.
The type 2 intramolecular Diels-Alder (IMDA) reaction is a valuable method for synthesis of both carbocyclic and heterocyclic bridged bicyclo[5.3.1]undecane and bicyclo[4.3.1]decane ring systems. These structures are common to a number of biologically important natural products. Asymmetric variants of the type 2 IMDA reaction incorporating oxazolidinone chiral auxiliaries have been evaluated. This study has resulted in systems that deliver bridged bicyclic [5.3.1] and [4.3.1] ring systems in high diastereomeric (97-99% de) and enantiomeric purity.
Brailsford
John A
JA
Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, CA 92697-2025, USA.
Zhu
Liang
L
Loo
Mandy
M
Shea
Kenneth J
KJ
D000473:Alkanes / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D001952:Bridged-Ring Compounds / Q000737:chemistry*; D008956:Models, Chemical; D013237:Stereoisomerism
D000473:Alkanes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D001952:Bridged-Ring Compounds; C022884:undecane; C012867:decane