Stereocontrolled construction of either stereoisomer of 12-oxatricyclo[6.3.1.0(2,7)]dodecanes using Prins-pinacol reactions.
[reaction: see text] 12-Oxatricyclo[6.3.1.0(2,7)]dodecanes can be efficiently synthesized in a stereoselective manner by Prins-pinacol reactions. By biasing the transition state of the Prins cyclization, it is possible to access either stereoisomer of this oxatricyclic ring system.
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025, USA. leoverma@uci.edu
Larry E
LE
Overman
Emile J
EJ
Velthuisen
D000473:Alkanes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D013237:Stereoisomerism
D000473:Alkanes; C007548:n-dodecane