Sterically biased 3,3-sigmatropic rearrangement of azides: Efficient preparation of nonracemic α-amino acids and heterocycles
(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.
Gagnon, David,Lauzon, Sophie,Godbout, Cedrickx,Spino, Claude
p. 4769 - 4771
(2007/10/03)
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