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1. Sterically biased 3,3-sigmatropic rearrangement of chiral allylic azides: application to the total syntheses of alkaloids

Author

Lauzon, Sophie, Tremblay, Francois, Gagnon, David, Godbout, Cedrickx, Chabot, Christine, Mercier-Shanks, Catherine, Perreault, Stephane, DeSeve, Helene, and Spino, Claude

Subjects
Alkaloids -- Chemical properties, Alkaloids -- Structure, Allylic compounds -- Chemical properties, Allylic compounds -- Structure, Biological sciences, Chemistry
Abstract

A tandem Mitsunobu/3,3-sigmatropic rearrangement of allylic azides on a chiral auxiliary system that favors one regioisomer is described. The sequence is completed by the oxidative cleavage of the auxiliary or by a ring-closing metathesis reaction that has produced a carbo- or heterocycle directly and a recyclable form of the chiral auxiliary.

Published
2008

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