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Stereoselective Strecker and Carbamate Annulation Methodology for the Synthesis of 1‐Amino‐1,2,5‐trideoxy‐2,5‐imino‐ L ‐iditol
Author(s) -
WinMason Anna L.,
Dangerfield Emma M.,
Tyler Peter C.,
Stocker Bridget L.,
Timmer Mattie S. M.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100523
Subject(s) - annulation , chemistry , strecker amino acid synthesis , carbamate , stereoselectivity , iodide , stereochemistry , organic chemistry , combinatorial chemistry , catalysis , enantioselective synthesis
An efficient and highly stereoselective synthesis of L ‐ ido ‐aminoiminosugar 3 has been described. Key in the synthesis is the application of a diastereoselective Strecker reaction and the extension of our carbamate annulation methodology to protected and functionalized alkenylamines. In addition, the identification of the primary iodide as a key intermediate during the carbamate annulation reaction provides insight into the mechanism of this reaction.