Journal
TETRAHEDRON
Volume 56, Issue 3, Pages 381-387Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(99)01025-X
Keywords
chlorosulfonyl isocyanate; nitrogen mustards; amino acids; Mitsunobu reaction; cyclosulfamides; 4-substituted-1,2,5-thiadiazolidine 1,1-dioxides
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We report here a practical access to a series of five-membered cyclosulfamides (1,2,5-thiadiazolidines 1,1-dioxides) N-2 substituted by the BOC group. These compounds are synthesized starting from chlorosulfonyl isocyanate and nitrogen mustards or amino acids. The derivatization of amino acids can lead to an alkyl group on C-4 with a well-defined configuration; in this case the N' position was protected by a benzyl group. These compounds are valuable tools for asymmetric synthesis. (C) 2000 Elsevier Science Ltd. All rights reserved.
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