Cyclopropane structural units from homoaldol adducts.
[reaction: see text] An efficient two-step homologation of aldehydes to cyclopropylaldehydes has been developed. Activation of homoaldol adducts derived from O-enecarbamates and N-enecarbamates provided high yields of cyclopropylaldehydes with good to excellent levels of trans/cis selectivity. Trapping of the intermediate oxonium ion and iminium ion intermediates has also been demonstrated, leading to direct isolation of cyclopropyl carbinol and cyclopropylamine products.
Taylor
Richard E
RE
Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556-5670, USA. taylor.61@nd.edu
Risatti
Christina A
CA
Engelhardt
F Conrad
FC
Schmitt
Michael J
MJ