TY - JOUR
T1 - First report of syn isomers in the diastereoselective synthesis of highly functionalized piperidines catalysed by wet picric acid
T2 - Factors influencing the syn-anti ratios
AU - Mukhopadhyay, Chhanda
AU - Rana, Sunil
AU - Butcher, Ray J.
AU - Schmiedekamp, Ann Marie
N1 - Funding Information:
One of the authors (S.R.) thanks the Council of Scientific and Industrial Research, New Delhi, for his fellowship (SRF). We thank the CAS Instrumentation Facility, Department of Chemistry, University of Calcutta for spectral data. We also acknowledge grant received from UGC funded Major project, F. No. 37-398 / 2009 (S.R.) dated 11-01-2010. The authors acknowledge computer use of the Lion-X series of computational clusters of the Research Computing and Cyber infrastructure group, a unit of Information Technology Services at Penn State University.
PY - 2011/11/2
Y1 - 2011/11/2
N2 - This is the first report of the formation of a syn-diastereoisomer in the diastereoselective synthesis of highly functionalized piperidines catalysed by wet picric acid via a one-pot, step-economic condensation of aromatic aldehydes, 1,3-dicarbonyl compounds and aromatic amines. DFT calculation shows that anti isomers are more stable compared to the syn. The syn-anti ratio of the products depends on the temperature and the nature of substitution on both the aromatic aldehydes and aromatic amines. Conditions for getting pure anti and pure syn compounds have been studied.
AB - This is the first report of the formation of a syn-diastereoisomer in the diastereoselective synthesis of highly functionalized piperidines catalysed by wet picric acid via a one-pot, step-economic condensation of aromatic aldehydes, 1,3-dicarbonyl compounds and aromatic amines. DFT calculation shows that anti isomers are more stable compared to the syn. The syn-anti ratio of the products depends on the temperature and the nature of substitution on both the aromatic aldehydes and aromatic amines. Conditions for getting pure anti and pure syn compounds have been studied.
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U2 - 10.1016/j.tetlet.2011.08.140
DO - 10.1016/j.tetlet.2011.08.140
M3 - Article
AN - SCOPUS:80054975647
SN - 0040-4039
VL - 52
SP - 5835
EP - 5840
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 44
ER -