Abstract
The first efficient synthesis of enantiopure homoketopinic acid, an interesting camphor derivative is firstly reported. The synthetic procedure uses 10-(triflyloxy)camphor as key electrophilic intermediate. The ability of 10-(triflyloxy)camphor to react selectively with a charged C-nucleophile (cyanide anion) without undergoing Grob fragmentation of the norbornane framework is also demonstrated.
Keywords: Bicyclic compounds, camphor derivatives, carboxylic acid, chiral agents
Letters in Organic Chemistry
Title: First Efficient Synthesis of Enantiopure Homoketopinic Acid
Volume: 4 Issue: 2
Author(s): Antonio Garcia Martinez, Santiago de la Moya Cerero, Enrique Teso Vilar, Amelia Garcia Fraile, Cristina Diaz Morillo and Tomas de las Casas Engel
Affiliation:
Keywords: Bicyclic compounds, camphor derivatives, carboxylic acid, chiral agents
Abstract: The first efficient synthesis of enantiopure homoketopinic acid, an interesting camphor derivative is firstly reported. The synthetic procedure uses 10-(triflyloxy)camphor as key electrophilic intermediate. The ability of 10-(triflyloxy)camphor to react selectively with a charged C-nucleophile (cyanide anion) without undergoing Grob fragmentation of the norbornane framework is also demonstrated.
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Cite this article as:
Martinez Antonio Garcia, de la Moya Cerero Santiago, Teso Vilar Enrique, Garcia Fraile Amelia, Diaz Morillo Cristina and de las Casas Engel Tomas, First Efficient Synthesis of Enantiopure Homoketopinic Acid, Letters in Organic Chemistry 2007; 4 (2) . https://dx.doi.org/10.2174/157017807780414208
DOI https://dx.doi.org/10.2174/157017807780414208 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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