First report of syn isomers in the diastereoselective synthesis of highly functionalized piperidines catalysed by wet picric acid: Factors influencing the syn-anti ratios

Chhanda Mukhopadhyay, Sunil Rana, Ray J. Butcher, Ann Marie Schmiedekamp

Research output: Contribution to journalArticle

55 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)5835-5840
Number of pages6
JournalTetrahedron Letters
Volume52
Issue number44
DOIs
StatePublished - Nov 2 2011

Fingerprint

Piperidines
Aldehydes
Isomers
Amines
Discrete Fourier transforms
Condensation
Substitution reactions
Economics
Temperature
picric acid

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

@article{40e0c687c5bb4364a36af8489eedf0aa,
title = "First report of syn isomers in the diastereoselective synthesis of highly functionalized piperidines catalysed by wet picric acid: Factors influencing the syn-anti ratios",
abstract = "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.",
author = "Chhanda Mukhopadhyay and Sunil Rana and Butcher, {Ray J.} and Schmiedekamp, {Ann Marie}",
year = "2011",
month = "11",
day = "2",
doi = "10.1016/j.tetlet.2011.08.140",
language = "English (US)",
volume = "52",
pages = "5835--5840",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "44",

}

First report of syn isomers in the diastereoselective synthesis of highly functionalized piperidines catalysed by wet picric acid : Factors influencing the syn-anti ratios. / Mukhopadhyay, Chhanda; Rana, Sunil; Butcher, Ray J.; Schmiedekamp, Ann Marie.

In: Tetrahedron Letters, Vol. 52, No. 44, 02.11.2011, p. 5835-5840.

Research output: Contribution to journalArticle

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

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.

UR - http://www.scopus.com/inward/record.url?scp=80054975647&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80054975647&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2011.08.140

DO - 10.1016/j.tetlet.2011.08.140

M3 - Article

AN - SCOPUS:80054975647

VL - 52

SP - 5835

EP - 5840

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 44

ER -