title: Stereocontrol in asymmetric S(E)' reactions of γ-substituted α,β-unsaturated aldehydes.
abstract: Asymmetric SE' reactions of (E)- and (Z)-γ-substituted-α,β-unsaturated aldehydes have been studied for the stereocontrolled preparation of nonracemic alcohols. Mild exchange reactions of allylic stannanes provide access to chiral 1,3-bis(tolylsulfonyl)-4,5-diphenyl-1,3-diaza-2-borolidines. These reagents display reactivity with the γ-substituted α,β-unsaturated aldehydes, which is characterized by matched and mismatched elements of stereocontrol. Computational analysis (using density functional theory) provides valuable insights to guide reaction development.
authors.affiliation: Department of Chemistry, Indiana University , Bloomington, Indiana 47405, United States .
authors.forename: David R
authors.initials: DR
authors.lastname: Williams
authors.forename: Bruce A
authors.initials: BA
authors.lastname: Atwater
authors.forename: Seth A
authors.initials: SA
authors.lastname: Bawel
authors.forename: Pucheng
authors.initials: P
authors.lastname: Ke
authors.forename: Osvaldo
authors.initials: O
authors.lastname: Gutierrez
authors.forename: Dean J
authors.initials: DJ
authors.lastname: Tantillo