An asymmetric synthesis of (R)-3-heterocyclic-substituted alanines starting from (2S)-(+)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (Schollkopf reagent) and heteroaromatic halogenomethyl derivatives via hydrolysis of intermediate adducts is reported. The diastereocontrolled addition gives mainly compounds with the (2S,5R) configuration whose formation is explained on the basis of the accepted model for the alkylation reaction of the Schollkopf reagent, and structure confirmed by spectroscopic data. Copyright (C) 2000 Elsevier Science Ltd.

Stereoselective synthesis of 3-heteroaromatic-substituted alanines / P. Dalla Croce, C. La Rosa, E. Pizzatti. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 11:12(2000), pp. 2635-2642. [10.1016/S0957-4166(00)00223-8]

Stereoselective synthesis of 3-heteroaromatic-substituted alanines

P. Dalla Croce
Primo
;
C. La Rosa
Secondo
;
2000

Abstract

An asymmetric synthesis of (R)-3-heterocyclic-substituted alanines starting from (2S)-(+)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (Schollkopf reagent) and heteroaromatic halogenomethyl derivatives via hydrolysis of intermediate adducts is reported. The diastereocontrolled addition gives mainly compounds with the (2S,5R) configuration whose formation is explained on the basis of the accepted model for the alkylation reaction of the Schollkopf reagent, and structure confirmed by spectroscopic data. Copyright (C) 2000 Elsevier Science Ltd.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/190249
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