title: Mechanistic rationalization of organocatalyzed conjugate addition of linear aldehydes to nitro-olefins.
abstract: Kinetic studies of the conjugate addition of propanal to nitrostyrene catalyzed by diarylprolinol ethers reveal that formation of the product iminium species is rate-determining and is promoted by both the reaction product and acid additives. The beneficial role of a dominant cyclobutane intermediate in maintaining high stereoselectivity is highlighted. This mechanistic understanding led to the design of highly productive reaction protocols.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, USA.
authors.forename: Jordi
authors.initials: J
authors.lastname: Burés
authors.forename: Alan
authors.initials: A
authors.lastname: Armstrong
authors.forename: Donna G
authors.initials: DG
authors.lastname: Blackmond