The enantioselective synthesis of 2-amino-3-hydroxynorbornene-2-carboxylic acid derivatives (5) was studied using the Diels-Alder reaction between cyclopentadiene and different dienophiles, i.e., alkyl 5-oxo-2-phenyloxazol-4-methylenecarbonates (1) or 2-benzoylamino-3-alkoxycarbonyloxy-acrylates (12), operating with different Lewis acids and both with thermal and with ultrasound conditions. The enantioselective Synthesis of the exo/endo compounds 5c,d and 5′c,d was achieved starting from the chiral menthyl acrylates 12b,c using Mg(ClO4)2 as the catalyst and ultrasound. The cycloadducts were obtained in very good yield, in mild conditions, in short time, and in good diastereomeric excess (exo, 80%; endo, 87%). Finally, the use of alkylidene-oxazolones or acrylates and EtAlCl2 or Mg(ClO4)2 as the catalyst allowed control of the cycloaddition reaction in favor of the exo or endo products.

Asymmetric Synthesis of 2-Amino-3-hydroxynorbornene-2-carboxylic Acids Derivatives / G. Abbiati, F. Clerici, M.L. Gelmi, A. Gambini, T. Pilati. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 66:19(2001 Sep 21), pp. 6299-6304.

Asymmetric Synthesis of 2-Amino-3-hydroxynorbornene-2-carboxylic Acids Derivatives

G. Abbiati
Primo
;
F. Clerici
Secondo
;
M.L. Gelmi;
2001-09-21

Abstract

The enantioselective synthesis of 2-amino-3-hydroxynorbornene-2-carboxylic acid derivatives (5) was studied using the Diels-Alder reaction between cyclopentadiene and different dienophiles, i.e., alkyl 5-oxo-2-phenyloxazol-4-methylenecarbonates (1) or 2-benzoylamino-3-alkoxycarbonyloxy-acrylates (12), operating with different Lewis acids and both with thermal and with ultrasound conditions. The enantioselective Synthesis of the exo/endo compounds 5c,d and 5′c,d was achieved starting from the chiral menthyl acrylates 12b,c using Mg(ClO4)2 as the catalyst and ultrasound. The cycloadducts were obtained in very good yield, in mild conditions, in short time, and in good diastereomeric excess (exo, 80%; endo, 87%). Finally, the use of alkylidene-oxazolones or acrylates and EtAlCl2 or Mg(ClO4)2 as the catalyst allowed control of the cycloaddition reaction in favor of the exo or endo products.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/156404
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