Competitive cationic pathways and the asymmetric synthesis of aryl-substituted cyclopropanes.
[reaction: see text] 1,2-Disubstituted cyclopropanes were synthesized in a nonracemic fashion via activation of the corresponding homoallylic alcohols in excellent yields. A series of substituted phenyl rings showed higher enantiospecificity for the cyclization as the electron-withdrawing ability of the group increased. The results offer strong support for the existence of competing cation mechanisms.
Melancon
Bruce J
BJ
Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556-5670, USA.
Perl
Nicholas R
NR
Taylor
Richard E
RE
D000438:Alcohols / Q000737:chemistry; D001965:Bromides / Q000737:chemistry; D002412:Cations / Q000737:chemistry*; D003521:Cyclopropanes / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D001965:Bromides; D002412:Cations; D003521:Cyclopropanes