Events The 4th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 4th International Electronic Conference on Synthetic Organic Chemistry

Published date

11 Sep, 2000

Citation

Carmen Najera, Patricia Mazon, Nuria Galindo, Rafael Chinchilla, Asymmetric Synthesis of Functionalized Prolines by Diastereoselective 1,3-Dipolar Cycloaddition Using Chiral Oxazinone Derivatives, in Proceedings of The 4th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2000, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-4-01802

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Asymmetric Synthesis of Functionalized Prolines by Diastereoselective 1,3-Dipolar Cycloaddition Using Chiral Oxazinone Derivatives

Rafael Chinchilla ¹

Nuria Galindo ¹

Patricia Mazon ¹

Carmen Najera ¹

1. Departamento de Quimica Organica, Universidad de Alicante. E-03080 Alicante, Spain

Abstract

The reaction of (5S,6S)-6-isopropyl-5-phenyl-1,4-oxazin-2-ones from glycine and alanine with formaldehyde in the presence of electron-deficient olefins afforded the corresponding adducts obtained by a diastereoselective 1,3-dipolar cycloaddition of the chiral azomethine ylids. Hydrolysis of these adducts allows the synthesis of enantiomerically enriched functionalized prolines

Keywords

Amino acids

oxazinones

1,3-dipolar cycloadditions

prolines

Arene-Catalysed Reductive Cleavage of the Benzylic Carbon-Sulfur Bond: Generation of Benzylic Lithium Reagents.

Efficient allylation of 4-silyloxy quinolinium triflates and other positively charged heteroaromatic systems