Stereochemistry associated with the addition of 2-(trimethylsilyl) thiazole to differentially protected. alpha.-amino aldehydes. Applications toward the synthesis of …

A Dondoni, G Fantin, M Fogagnolo…

Index: Dondoni, Alessandro; Fantin, Giancarlo; Fogagnolo, Marco; Pedrini, Paola Journal of Organic Chemistry, 1990 , vol. 55, # 5 p. 1439 - 1446

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Citation Number: 148

Abstract

The stereochemistry and synthetic utility of the addition of 2-(trimethylsily1) thiazole (2-TST, 1) to various N-protected a-amino aldehydes is described. The reactions of 1 with N-Boc-L- serinal acetonide (2) and N-Boc-L-threoninal acetonide (3) are essentially anti diastereoselective (ds= 85-90%) in agreement with the Felkin-Anh model for asymmetric induction, whereas the reactions with 0-benzyl-NH-Boc-L-serinal (4) and NH-Boc-L- ...

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