Menthone and p-menthyl-3-carboxaldehyde as chiral auxiliaries

Claude Spino

doi:10.1039/C0CC05543C

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Chemical Communications

Issue 17, 2011

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Menthone and p-menthyl-3-carboxaldehyde as chiral auxiliaries

Claude Spino

Chem. Commun., 2011,47, 4872-4883

DOI: 10.1039/C0CC05543C
Received 13 Dec 2010, Accepted 15 Feb 2011
First published on the web 09 Mar 2011

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Abstract
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Two chiral auxiliaries and the role they play in the preparation of chiral carbonyl compounds and heterocyclic compounds are presented. Key reactions include S_N2′ displacements, Mitsunobu with hydrazoic acid, and 3,3-sigmatropic rearrangements. One of the auxiliaries serves many functions and is removed either by oxidative cleavage or RCM reaction.

Abstract from Methods in Organic Synthesis 2011

A review, with 70 references, discussing the use of the title compounds as chiral auxiliaries in the synthesis of chiral carbonyl compounds and heterocycles.

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