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Stereocontrolled Synthesis of β‐Amino Alcohols from Lithiated Aziridines and Boronic Esters
Author(s) -
Schmidt Frank,
Keller Florian,
Vedrenne Emeline,
Aggarwal Varinder K.
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200805272
Subject(s) - regioselectivity , lithium (medication) , aryl , chemistry , base (topology) , organic chemistry , combinatorial chemistry , catalysis , mathematics , psychology , mathematical analysis , alkyl , psychiatry
β‐Amino alcohols have been prepared with high selectivity by the addition of lithiated aziridines to boronic esters. The regioselectivity of lithiation for aryl aziridines is sensitive to the reaction conditions and to the base employed. This response was exploited to give either class of β‐amino alcohols (see scheme; Boc= tert ‐butoxycarbonyl, Bus= tert ‐butylsulfonyl, LTMP=lithium 2,2,6,6‐tetramethylpiperidide, pin=pinacolato).