Asymmetric synthesis of 2-amino-3-hydroxynorbornene-2-carboxylic acid derivatives.

doi:10.1021/JO010374Q

Paper

Asymmetric synthesis of 2-amino-3-hydroxynorbornene-2-carboxylic acid derivatives.

Published Aug 24, 2001 · G. Abbiati, F. Clerici, M. Gelmi

The Journal of organic chemistry

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19

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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(ClO(4))(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 EtAlCl(2) or Mg(ClO(4))(2) as the catalyst allowed control of the cycloaddition reaction in favor of the exo or endo products.

Study Snapshot

Enantioselective synthesis of 2-amino-3-hydroxynorbornene-2-carboxylic acid derivatives using ultrasound and chiral menthyl acrylates allows for rapid, mild, and diastereomeric excess production of exo and endo products.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Asymmetric synthesis of 2-amino-3-hydroxynorbornene-2-carboxylic acid derivatives.

References

Citations

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