Synthesis 2018; 50(09): 1841-1848
DOI: 10.1055/s-0037-1609224
paper
© Georg Thieme Verlag Stuttgart · New York

Noscapine Derivatives as New Chiral Catalysts in Asymmetric Synthesis­: Highly Enantioselective Addition of Diethylzinc to Aldehydes­

Maryam Mohebbi
a   Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, 1983963113 Tehran, Iran   eMail: p-salehi@sbu.ac.ir
,
Morteza Bararjanian
a   Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, 1983963113 Tehran, Iran   eMail: p-salehi@sbu.ac.ir
,
Samad N. Ebrahimi
a   Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, 1983963113 Tehran, Iran   eMail: p-salehi@sbu.ac.ir
,
Martin Smieško
b   Division of Molecular Modeling, Department of Pharmaceutical Sciences, University of Basel, Klingelbergstrasse 50, 4056 Basel, Switzerland
,
a   Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, 1983963113 Tehran, Iran   eMail: p-salehi@sbu.ac.ir
› Institutsangaben
The authors would like to thank the Iran National Science Foundation (INSF, grant number 94-S-43569) for financial support of the work.
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Publikationsverlauf

Received: 01. Januar 2018

Accepted after revision: 09. Januar 2018

Publikationsdatum:
05. Februar 2018 (online)


Abstract

Noscapine, a natural alkaloid, has never been used as a parent scaffold in chiral induction. The first examples of noscapinoid compounds as efficient catalysts in asymmetric synthesis are now reported. Three derivatives of noscapine were synthesized from its reaction with different Grignard reagents. Asymmetric addition of diethylzinc to aldehydes­ was performed in the presence of these catalysts in high yields and good to excellent ees.

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