868744-81-4Relevant articles and documents
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.
Sterically biased 3,3-sigmatropic rearrangement of azides: Efficient preparation of nonracemic α-amino acids and heterocycles
Gagnon, David,Lauzon, Sophie,Godbout, Cedrickx,Spino, Claude
, p. 4769 - 4771 (2007/10/03)
(Chemical Equation Presented) Homochiral α-amino acids, heterocycles, and carbocycles are efficiently constructed via a short sequence of reactions starting from the chiral auxiliary p-menthane-3-carboxaldehyde. The key feature of the sequence is a highly selective tandem Mitsunobu/3,3-sigmatropic rearrangement of hydrazoic acid that procures enantiomerically enriched allylic azides. The sequence is either terminated by oxidative cleavage to provide amino acids or by ring-closing metathesis to provide heterocycles or carbocycles bearing nitrogen.