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

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

Two chiral auxiliaries and the role they play in the preparation of chiral carbonyl compounds and heterocyclic compounds are presented. Key reactions include S(N)2' displacements, Mitsunobu with hydrazoic acid, and 3,3-sigmatropic rearrangements. One of the auxiliaries serves many functions and...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2011-01, Vol.47 (17), p.4872-4883
1. Verfasser: Spino, Claude
Format: Artikel
Sprache:eng
Schlagworte:
Carbonyl compounds
Cleavage
Heterocyclic compounds
Hydrazoic acid
RCM
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Beschreibung
Zusammenfassung:Two chiral auxiliaries and the role they play in the preparation of chiral carbonyl compounds and heterocyclic compounds are presented. Key reactions include S(N)2' 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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c0cc05543c