Role of 2-oxonia Cope rearrangements in Prins cyclization reactions.
[reaction--see text] The 2-oxonia Cope rearrangement is undetectable in typical Prins cyclization reactions. We have investigated the Cope rearrangement in a Prins cyclization reaction using a competitive reduction of the oxocarbenium ion intermediate, and a racemization reaction mediated by the rearrangement. In our unactivated substrate, the 2-oxonia Cope rearrangement was much faster than Prins cyclization. An enantioselective allyl transfer reaction also was developed using a 2-oxonia Cope rearrangement.
Rychnovsky
S D
SD
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025, USA. srychnov@uci.edu
Marumoto
S
S
Jaber
J J
JJ
D000498:Allyl Compounds / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D013237:Stereoisomerism
D000498:Allyl Compounds; D001555:Benzene Derivatives