Tetrahedron: Asymmetry

Enantioselective synthesis of unsaturated amino acids using p-methoxybenzylamine as an ammonia equivalent

M Alcón, A Moyano, MA Pericàs, A Riera

文献索引：Alcon, Montserrat; Moyano, Albert; Pericas, Miquel A.; Riera, Antoni Tetrahedron Asymmetry, 1999 , vol. 10, # 23 p. 4639 - 4651

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被引用次数: 38

摘要

A versatile, non-alkylative enantioselective synthesis of unsaturated α-amino acids based on the Sharpless asymmetric epoxidation has been developed. Enantiomerically enriched trans epoxy alcohols bearing unsaturated substituents were prepared and submitted to regio-and stereospecific ring-opening with p-methoxybenzylamine as a nucleophile, leading to anti-3- (p-methoxybenzylamino)-1, 2-diols which were further protected by reaction with Boc2O. ...