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One‐Pot Tandem Strecker Reaction and Iminocyclisations: Syntheses of Trihydroxypiperidine α‐Iminonitriles
Author(s) -
Ayers Benjamin J.,
Fleet George W. J.
Publication year - 2014
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.201301705
Subject(s) - chemistry , strecker amino acid synthesis , pyrrolidine , tandem , organic chemistry , cascade reaction , reaction conditions , stereochemistry , catalysis , enantioselective synthesis , composite material , materials science
Unbranched, and α‐ and β‐methyl‐branched, trihydroxypiperidine α‐iminonitriles have been obtained in a single step from protected 5‐ O ‐tosylate pentoses. This reaction comprises a one‐pot tandem Strecker reaction and iminocyclisation. These trihydroxypiperidine α‐iminonitriles are precursors to trihydroxypipecolic acids. No formation of pyrrolidine products was observed.