‘One-pot’ organocatalyzed enantioselective synthesis of highly functionalized 3,4,5,6-tetrasubstituted dihydropyrans by sequential Knoevenagel condensation/Michael addition and hemiacetalization

Ajay R. Tilekar; Arun R. Jagdale; Gagan Kukreja; G. Gautham Shenoy; Neelima Sinha

doi:10.1016/j.tetasy.2016.10.014

‘One-pot’ organocatalyzed enantioselective synthesis of highly functionalized 3,4,5,6-tetrasubstituted dihydropyrans by sequential Knoevenagel condensation/Michael addition and hemiacetalization

Ajay R. Tilekar, Arun R. Jagdale, Gagan Kukreja, G. Gautham Shenoy, Neelima Sinha

Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

An organocatalytic ‘one-pot’ synthesis of highly functionalized 3,4,5,6-tetrasubstituted dihydropyrans has been developed. Excellent enantio- and diastereo selectivity with good yields are some of the salient features of this methodology. This reaction takes advantage of proline based catalysts and follows stepwise sequential transformations including Knoevenagel condensation–Michael addition–hemiacetalization towards the synthesis of complex dihydropyranol framework.

Original language	English
Pages (from-to)	153-161
Number of pages	9
Journal	Tetrahedron Asymmetry
Volume	28
Issue number	1
DOIs	https://doi.org/10.1016/j.tetasy.2016.10.014
Publication status	Published - 2017

All Science Journal Classification (ASJC) codes

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/j.tetasy.2016.10.014

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title = "{\textquoteleft}One-pot{\textquoteright} organocatalyzed enantioselective synthesis of highly functionalized 3,4,5,6-tetrasubstituted dihydropyrans by sequential Knoevenagel condensation/Michael addition and hemiacetalization",

abstract = "An organocatalytic {\textquoteleft}one-pot{\textquoteright} synthesis of highly functionalized 3,4,5,6-tetrasubstituted dihydropyrans has been developed. Excellent enantio- and diastereo selectivity with good yields are some of the salient features of this methodology. This reaction takes advantage of proline based catalysts and follows stepwise sequential transformations including Knoevenagel condensation–Michael addition–hemiacetalization towards the synthesis of complex dihydropyranol framework.",

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journal = "Tetrahedron Asymmetry",

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‘One-pot’ organocatalyzed enantioselective synthesis of highly functionalized 3,4,5,6-tetrasubstituted dihydropyrans by sequential Knoevenagel condensation/Michael addition and hemiacetalization. / Tilekar, Ajay R.; Jagdale, Arun R.; Kukreja, Gagan et al.

In: Tetrahedron Asymmetry, Vol. 28, No. 1, 2017, p. 153-161.

Research output: Contribution to journal › Article › peer-review

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AU - Tilekar, Ajay R.

AU - Jagdale, Arun R.

AU - Kukreja, Gagan

AU - Shenoy, G. Gautham

AU - Sinha, Neelima

PY - 2017

Y1 - 2017

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AB - An organocatalytic ‘one-pot’ synthesis of highly functionalized 3,4,5,6-tetrasubstituted dihydropyrans has been developed. Excellent enantio- and diastereo selectivity with good yields are some of the salient features of this methodology. This reaction takes advantage of proline based catalysts and follows stepwise sequential transformations including Knoevenagel condensation–Michael addition–hemiacetalization towards the synthesis of complex dihydropyranol framework.

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‘One-pot’ organocatalyzed enantioselective synthesis of highly functionalized 3,4,5,6-tetrasubstituted dihydropyrans by sequential Knoevenagel condensation/Michael addition and hemiacetalization

Abstract

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