Tetrahedron

Addition of a Reformatsky reagent to N-anthracene-9-sulfonyl and related imines: Synthesis of protected β-amino acids

AJ Robinson, PB Wyatt

Index: Robinson, Andrew J.; Wyatt, Peter B. Tetrahedron, 1993 , vol. 49, # 48 p. 11329 - 11340

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Citation Number: 18

Abstract

The Reformatsky reagent tert-butoxycarbonylmethylzinc bromide adds in high yields to N- sulfonylimines, eg 1a–1d, derived by condensation of benzaldehyde dimethyl acetal with methanesulfonamide, toluene-4-sulfonamide, 4-(methoxycarbonyl) benzenesulfonamide and sulfamide: the products are protected β-amino acids 2a–2d. N-Deprotection occurs reductively (Na-naphthalene; low yields) for 2b and 2c or hydrolytically (refluxing aq. ...