Synlett 2013; 24(18): 2401-2406
DOI: 10.1055/s-0033-1339943
letter
© Georg Thieme Verlag Stuttgart · New York

Catalytic Asymmetric Reduction of Prochiral Ketones with Chiral β-Amino Alcohol N-Boranes and the Corresponding Tris(oxazaborolidine)borazines

Afroditi Pinaka
a  Division of Physical Chemistry, NCSR Demokritos, 15310 Athens, Greece   Email: kyriakos@chem.demokritos.gr
b  Department of Chemical Engineering, NTU Athens, 15780 Athens, Greece
,
Dimitra Dimotikali
b  Department of Chemical Engineering, NTU Athens, 15780 Athens, Greece
,
Bezhan Chankvetadze
c  Institute of Physical and Analytical Chemistry, School of Exact and Natural Sciences,Tbilisi State University, 0170 Tbilisi, Georgia
,
Kyriakos Papadopoulos*
a  Division of Physical Chemistry, NCSR Demokritos, 15310 Athens, Greece   Email: kyriakos@chem.demokritos.gr
,
Georgios C. Vougioukalakis*
a  Division of Physical Chemistry, NCSR Demokritos, 15310 Athens, Greece   Email: kyriakos@chem.demokritos.gr
d  Department of Chemistry, University of Athens, 15771 Athens, Greece   Fax: +30(210)6511766   Email: vougiouk@chem.uoa.gr
› Author Affiliations
Further Information

Publication History

Received: 28 August 2013

Accepted after revision: 24 September 2013

Publication Date:
14 October 2013 (online)


Dedicated to Professor Nikos Hadjichristidis on the occasion of his 70th birthday

Abstract

Chiral β-amino alcohol-derived N-borane catalysts, namely noncyclic (2S)- and (2R)-2-amino-2-phenylethanol N-borane and their corresponding cyclic trimeric borazine derivatives, were synthesized and their catalytic activities in the asymmetric reduction of prochiral ketones were examined. Both the noncyclic and cyclic catalysts successfully catalyzed this reaction, giving the desired secondary alcohols in up to 82% isolated yield and with up to 80% enantioselectivity. The noncyclic catalyst was stable in aqueous and organic solvents, whereas the polycyclic borazine was stable only in nonprotic dry organic solvents.

Supporting Information

 
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