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Scheme 4 Synthesis of (S,S)-reboxetine (19).
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Scheme 5 Synthesis of (+)-epi-cytoxazone (21).
In summary, the (salen)Co(III)-catalyzed HKR of racemic
alkoxy- and azido epoxides provides a highy practical route to
enantiopure syn- or anti-alkoxy- and azido epoxides and the
corresponding 1,2-diols in a single step. The reaction is
convenient to carry out under mild conditions displaying a
wide range of substrate scope. We believe that this HKR
strategy will find applications in the field of asymmetric
synthesis of bioactive molecules owing to the flexible nature
of the synthesis of racemic alkoxy- and azido epoxides and the
ready availability of catalyst in both enantiomeric forms.
R.S.R and P.V.C. thank CSIR New Delhi, for the award of
senior research fellowships and DST (No. SR/S1/OC-72/2006)
New Delhi, for financial support. The authors are also thankful
to Dr B. D. Kulkarni, Head, Chemical Engineering and Process
Development Division, for his constant encouragement.
(h) D. M. Aparicio, D. Gnecco, A. Galindo, J. R. Jua
M. L. Orea, A. Mendoza and J. L. Teran, Tetrahedron: Asymme-
try, 2009, 20, 2764–68.
´
rez,
´
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This journal is The Royal Society of Chemistry 2010
5014 | Chem. Commun., 2010, 46, 5012–5014