A general approach to high-yielding asymmetric synthesis of chiral 3-alkyl-4-nitromethylchromans via cascade Barbas–Michael and acetalization reactions

Dhevalapally B. Ramachary; M. Shiva Prasad; R. Madhavachary

doi:10.1039/C0OB00861C

A general approach to high-yielding asymmetric synthesis of chiral 3-alkyl-4-nitromethylchromans via cascade Barbas–Michael and acetalization reactions

Dhevalapally B. Ramachary,*^a M. Shiva Prasad^a and R. Madhavachary^a

* Corresponding authors

^a School of Chemistry, University of Hyderabad, Hyderabad, India
E-mail: ramsc@uohyd.ernet.in
Fax: +91-40-23012460

Abstract

A general approach to the high-yielding asymmetric synthesis of chiral 3-alkyl-4-nitromethylchromans as drug intermediates was achieved through cascade Barbas–Michael and acetalization (BMA) reactions on 2-(2-nitrovinyl)phenols with aldehydes in the presence of a catalytic amount of (R)-DPPOTMS and PhCO₂H. Herein, we have also demonstrated the application of chiral BMA products in the synthesis of functionalized chromanes and chromenes in very good yields with high optical purity, which are very useful compounds in medicinal chemistry.

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Publication details

The article was received on 11 Oct 2010, accepted on 11 Jan 2011 and first published on 03 Mar 2011

Article type: Paper

DOI: 10.1039/C0OB00861C

Citation: Org. Biomol. Chem., 2011,9, 2715-2721

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A general approach to high-yielding asymmetric synthesis of chiral 3-alkyl-4-nitromethylchromans via cascade Barbas–Michael and acetalization reactions

D. B. Ramachary, M. Shiva Prasad and R. Madhavachary, Org. Biomol. Chem., 2011, 9, 2715
DOI: 10.1039/C0OB00861C
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Organic & Biomolecular Chemistry

A general approach to high-yielding asymmetric synthesis of chiral 3-alkyl-4-nitromethylchromans via cascade Barbas–Michael and acetalization reactions

Abstract

Supplementary files

Publication details

A general approach to high-yielding asymmetric synthesis of chiral 3-alkyl-4-nitromethylchromans via cascade Barbas–Michael and acetalization reactions

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