Stereocontrol in asymmetric S(E)' reactions of -substituted ,-unsaturated aldehydes. Academic Article

abstract

• Asymmetric SE' reactions of (E)- and (Z)--substituted-,-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 -substituted ,-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

• Gutierrez Santacruz, Osvaldo

published proceedings

• Org Lett

author list (cited authors)

• Williams, D. R., Atwater, B. A., Bawel, S. A., Ke, P., Gutierrez, O., & Tantillo, D. J.

citation count

• 5

complete list of authors

• Williams, David R||Atwater, Bruce A||Bawel, Seth A||Ke, Pucheng||Gutierrez, Osvaldo||Tantillo, Dean J

publication date

• January 2014

publisher

• American Chemical Society (ACS)  Publisher

published in

• Organic Letters  Journal

PubMed Central ID

• 24377373

Digital Object Identifier (DOI)

• 10.1021/ol403351x

start page

• 468

end page

• 471

volume

• 16

issue

• 2

URL

• http://dx.doi.org/10.1021/ol403351x