Events The 8th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

10.3390/ecsoc-8-01937

This submission belongs to the session a. General Organic Synthesis of the event The 8th International Electronic Conference on Synthetic Organic Chemistry

Published date

01 Nov, 2004

Citation

Antonio García Martínez, Enrique Teso Vilar, Amelia García Fraile, Cristina Diaz Morillo, Santiago de la Moya Cerero, Enantiospecific Preparation of 10-(pyperidin-1-yl)Camphor: A Model Procedure for 10-Aminocamphors, in Proceedings of The 8th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2004, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-8-01937

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Enantiospecific Preparation of 10-(pyperidin-1-yl)Camphor: A Model Procedure for 10-Aminocamphors

Antonio García Martínez ¹

Enrique Teso Vilar ²

Amelia García Fraile ²

Cristina Diaz Morillo ²

Santiago de la Moya Cerero ¹

1. Universidad Complutense de Madrid, Departamento de Química Orgánica I, Ciudad Universitaria s/n, 28040 Madrid, Spain

2. Universidad Nacional de Educación a Distancia, Senda del Rey 9, 28040 Madrid, Spain

Abstract

Enantiopure (1R)-10-(pyperidin-1-yl)camphor has been straightforwardly obtained from natural camphor in five individual steps and with a high overall yield. The process involves a stereocontrolled double-Wagner-Meerwein-rearrangement strategy to generate 10-(triflyloxy)camphor as the key intermediate. This peculiarly-stable neopentylic-like triflate is able to react with pyperidine easily and without producing Grob-like fragmentation of the b-(triflyloxy)ketone-based norbornane system. The described procedure constitutes a model procedure for the sterecontrolled preparation of interesting 10-aminocamphors.

Keywords

n/a

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