Dauben–Michno oxidative transposition of allylic cyanohydrins — Enantiomeric switch of (–)-carvone to (+)-carvone*Based on the 2010 Bader Award Lecture.-Reference-Cited by-同舟云学术

Dauben–Michno oxidative transposition of allylic cyanohydrins — Enantiomeric switch of (–)-carvone to (+)-carvone*Based on the 2010 Bader Award Lecture.

Published:2011-05 Issue:5 Volume:89 Page:535-543
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Hudlicky Jason R.¹,Werner Lukas¹,Semak Vladislav¹,Simionescu Razvan¹,Hudlicky Tomas¹

Affiliation:

1. Department of Chemistry and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines, ON L2S 3A1, Canada.

Abstract

Allylic cyanohydrins were subjected to Dauben–Michno oxidation at low temperatures to provide β-cyanoenones in good to excellent yields. The potential of this oxidative transposition as a means of an enantiomeric switch of enones containing a latent plane of symmetry was tested by conversion of (–)-carvone to its enantiomer.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

http://www.nrcresearchpress.com/doi/pdf/10.1139/v11-026

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