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Selective Elaboration of Aminodiols towards Small Ring α‐ and β‐Amino Acid Derivatives that Incorporate an Aziridine, Azetidine, or Epoxide Scaffold
Author(s) -
Semina Elena,
Žukauskaitė Asta,
Šačkus Algirdas,
De Kimpe Norbert,
Mangelinckx Sven
Publication year - 2016
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.201600036
Subject(s) - azetidine , chemistry , aziridine , dihydroxylation , epoxide , ring (chemistry) , stereochemistry , hydroxylation , osmium , organic chemistry , combinatorial chemistry , enantioselective synthesis , catalysis , ruthenium , enzyme
The osmium‐catalyzed dihydroxylation of N ‐substituted alkyl 2‐(aminomethyl)acrylates resulted in the efficient synthesis of 2‐(aminomethyl)‐2,3‐dihydroxypropanoates in good yields (82–89 %). The resulting aminodiols were elaborated in a selective diversity‐oriented synthesis to produce the corresponding 2‐(aminomethyl)oxirane‐2‐carboxylates, functionalized aziridine‐2‐carboxylates, and azetidine‐3‐carboxylates by using straightforward reactions.