Synthesis and crystal structure of enantiopure N-tritylaziridin-2-ylmethanols from L-serine and L-threonine

…, JB Hammink, F áJan Dommerholt

Index: Willems, Johannes G. H.; Hersmis, Marco C.; De Gelder, Rene; Smits, Jan M. M.; Hammink, Jeannet B.; Dommerholt, F. Jan; Thijs, Lambertus; Zwanenburg, Binne Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 6 p. 963 - 967

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Citation Number: 38

Abstract

A convenient multigram 'one pot procedure'for the synthesis of methyl N-tritylaziridine-2- carboxylates 1 and 2, starting from the N-tritylmethyl esters of L-serine 9 and L-threonine 10 and using methanesulfonyl chloride and triethylamine, is described. The N-tritylaziridin-2- ylmethanols 3 and 4 are prepared from the corresponding methyl N-tritylaziridine-2- carboxylates 1 and 2 using a Grignard reaction. 1H and 13C NMR spectral and HPLC ...