Open AccessAminodiols via Stereocontrolled Oxidation of Methyleneaziridines
Author(s) -
Jared W. Rigoli,
Ilia A. Guzei,
Jennifer M. Schomaker
Publication year - 2014
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol5003576
Subject(s) - chemistry , vicinal , heteroatom , amine gas treating , bicyclic molecule , diol , stereochemistry , sequence (biology) , alcohol , combinatorial chemistry , organic chemistry , ring (chemistry) , biochemistry
A highly diastereoselective Ru-catalyzed oxidation/reduction sequence of bicyclic methyleneaziridines provides a facile route to complex 1-amino-2,3-diol motifs. The relative anti stereochemistry between the amine and the vicinal alcohol are proposed to result from 1,3-bischelation in the transition state by the C1 and C3 heteroatoms.
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