474380-45-5Relevant academic research and scientific papers
Increased Felkin-Anh selectivity in nucleophilic additions to α-chiral aldehydes using vinylalanes
Spino, Claude,Granger, Marie-Claude,Boisvert, Luc,Beaulieu, Christian
, p. 4183 - 4185 (2002)
Vinylalanes, prepared from the zirconium-catalyzed carboalumination of alkynes, were added directly to aldehydes bearing an alpha chiral carbon to give good yields of the corresponding alcohols. The addition was more stereoselective than the addition of t
Sterically biased 3,3-sigmatropic rearrangement of chiral allylic azides: Application to the total syntheses of alkaloids
Lauzon, Sophie,Tremblay, Francois,Gagnon, David,Godbout, Cedrickx,Chabot, Christine,Mercier-Shanks, Catherine,Perreault, Stephane,DeSeve, Helene,Spino, Claude
, p. 6239 - 6250 (2008/12/22)
(Chemical Equation Presented) We describe a tandem Mitsunobu/3,3- sigmatropic rearrangement of allylic azides on a chiral auxiliary system that favors one regioisomer thanks to its exceptional steric bias. The sequence may be completed by the oxidative cleavage of the auxiliary or by a ring-closing metathesis reaction that produces a carbo-or heterocycle directly and a recyclable form of the chiral auxiliary. Applications of the methodology to the total synthesis of (+)-coniine, (+)-lentiginosin, and (+)-pumiliotoxin C are reported.
p-menthane-3-carboxaldehyde: A useful chiral auxiliary for the synthesis of chiral quaternary carbons of high enantiomeric purity
Spino, Claude,Godbout, Cedrickx,Beaulieu, Christian,Harter, Magali,Mwene-Mbeja, Topwe M.,Boisvert, Luc
, p. 13312 - 13319 (2007/10/03)
(+)- or (-)-p-Menthane-S-carboxaldehyde is made in two easy steps from (+)- or (-)-menthone, respectively. This auxiliary allows for the synthesis of carbonyl compounds bearing a α-chiral quaternary carbon. The flexibility, efficiency, and ease of use of
Increased Felkin-Anh Selectivity Using AlMe3 in the Addition of Vinyllithiums to α-Chiral Aldehydes: Do "Ate" Complexes Play Any Role?
Spino, Claude,Granger, Marie-Claude,Tremblay, Marie-Claude
, p. 4735 - 4737 (2007/10/03)
(Matrix Presented) AlMe3 dramatically increases the diastereoselectivity of addition of vinyllithiums to α-chiral aldehydes but decreases that of methyllithium. Our results are explained in terms of an addition of the free vinyllithium on the M
