Synthetic access to α-substituted prop-2-ynylamines and α-acetylenic amino acids via the t-butyl N-trimethylsilylprop-2-ynylcarbamate dianion

BW Metcalf, P Casara

Index: Metcalf,B.W.; Casara,P. Journal of the Chemical Society, Chemical Communications, 1979 , p. 119 - 120

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Citation Number: 3

Abstract

WE recently reported that the alkylation reactions of the dianion derived from the acetylenic glycinate (la), with a variety of electrophiles, including a Michael acceptor, proceed invariably in a regiospecific sense to afford acetyl- enic and not allenic products.1 Such regiospecificity, ... SiMe, I i. me '1' ii. RZX @ ... When the t-butyl carbamate (3) is treated with an excess of lithium di-isopropylamide (LDA) or t-butyl-lithium in the presence of tetramethylethylenediamine at - 78 "C, the ...