Reaction between isocyanides and dialkyl acetylenedicarboxylates in the presence of 3-methylcyclopentane-1,2,4-trione. One-pot diastereoselective synthesis of tetrahydrocyclopenta[b]pyran derivatives

Issa Yavari; Mehdi Adib; Mohammad H. Sayahi

doi:10.1039/B207548M

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Reaction between isocyanides and dialkyl acetylenedicarboxylates in the presence of 3-methylcyclopentane-1,2,4-trione. One-pot diastereoselective synthesis of tetrahydrocyclopenta[b]pyran derivatives

Issa Yavari,*^a Mehdi Adib^a and Mohammad H. Sayahi^a

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* Corresponding authors

^a Department of Chemistry, University of Tarbiat Modarres, P. O. Box 14115-175, Tehran, Iran
E-mail: isayavar@yahoo.com
Fax: +98 21 8006544

Abstract

The reactive 1 ∶ 1 intermediate produced in the reaction between alkyl or aryl isocyanides and dialkyl acetylenedicarboxylates was trapped by 3-methylcyclopentane-1,2,4-trione to yield highly functionalized tetrahydrocyclopenta[b]pyran derivatives in excellent yields.

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DOI: https://doi.org/10.1039/B207548M
Article type: Communication
Submitted: 01 Aug 2002
Accepted: 23 Sep 2002
First published: 03 Oct 2002

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J. Chem. Soc., Perkin Trans. 1, 2002, 2343-2346

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Reaction between isocyanides and dialkyl acetylenedicarboxylates in the presence of 3-methylcyclopentane-1,2,4-trione. One-pot diastereoselective synthesis of tetrahydrocyclopenta[b]pyran derivatives

I. Yavari, M. Adib and M. H. Sayahi, J. Chem. Soc., Perkin Trans. 1, 2002, 2343 DOI: 10.1039/B207548M

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Journal of the Chemical Society, Perkin Transactions 1

Reaction between isocyanides and dialkyl acetylenedicarboxylates in the presence of 3-methylcyclopentane-1,2,4-trione. One-pot diastereoselective synthesis of tetrahydrocyclopenta[b]pyran derivatives

Abstract

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Reaction between isocyanides and dialkyl acetylenedicarboxylates in the presence of 3-methylcyclopentane-1,2,4-trione. One-pot diastereoselective synthesis of tetrahydrocyclopenta[b]pyran derivatives

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