Cyclic hydroxamates, especially multiply substituted [1, 2] oxazinan-3-ones

…, MH Cheng, GV Shustov, CI Akuche

Index: Wolfe, Saul; Wilson, Marie-Claire; Cheng, Ming-Huei; Shustov, Gennady V.; Akuche, Christiana I. Canadian Journal of Chemistry, 2003 , vol. 81, # 8 p. 937 - 960

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Citation Number: 28

Abstract

Routes to putative N-acyl-d-ala-d-ala surrogates, beginning with the conversion of 4-, 5-, and 6-membered lactones into 5-, 6-, and 7-membered cyclic hydroxamates, are reported. The key step of the synthesis is trimethylaluminium-promoted cyclization of an ω- aminooxyester. The 7-membered cyclic hydroxamate crystallizes in a chair conformation. Extension of the reaction sequence to homoserine or homoserine lactone leads to ...