1.
Org Lett
; 16(2): 468-71, 2014 Jan 17.
Artigo
em Inglês
| MEDLINE
| ID: mdl-24377373
RESUMO
Asymmetric SE' reactions of (E)- and (Z)-γ-substituted-α,ß-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,ß-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.