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

Maryam Mohebbi; Morteza Bararjanian; Samad N. Ebrahimi; Martin Smieško; Peyman Salehi

doi:10.1055/s-0037-1609224

Synthesis, Table of Contents

Synthesis 2018; 50(09): 1841-1848
DOI: 10.1055/s-0037-1609224

paper

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

Maryam Mohebbi

^aDepartment 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

^aDepartment 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

^aDepartment 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

^bDivision of Molecular Modeling, Department of Pharmaceutical Sciences, University of Basel, Klingelbergstrasse 50, 4056 Basel, Switzerland

,

Peyman Salehi *

^aDepartment of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, 1983963113 Tehran, Iran Email: p-salehi@sbu.ac.ir

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Abstract

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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.

Key words

noscapine - asymmetric reaction - diethylzinc - alkaloids - MacroModel

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References

References

1a Kitamura M. Suga S. Kawai K. Noyori R. J. Am. Chem. Soc. 1986; 108: 6071
1b Yamakawa M. Noyori R. J. Am. Chem. Soc. 1995; 117: 6327
1c Kitamura M. Suga S. Oka H. Noyori R. J. Am. Chem. Soc. 1998; 120: 9800

2a Zhang W. Tang R. Yu H. Gao S. Appl. Organomet. Chem. 2014; 28: 545
2b Faigl F. Erdelyi Z. Deak S. Nyerges M. Mátravölgyi B. Tetrahedron Lett. 2014; 55: 6891
2c Liu L. Long Q. Aoki T. Zhang G. Kaneko T. Teraguchi M. Zhang C. Wang Y. Chirality 2015; 27: 454
2d Zhang A.-l. Yang L.-w. Yang N.-f. Liu Y.-l. Tetrahedron: Asymmetry 2014; 25: 289

3a Tseng S.-L. Yang T.-K. Tetrahedron: Asymmetry 2004; 15: 3375
3b Anderson J. Chem. Commun. 1998; 393

4a Celik S. Cakici M. Kilic H. Sahin E. Tetrahedron: Asymmetry 2015; 26: 152
4b Gök Y. Kekeç L. Tetrahedron Lett. 2014; 55: 2727

5 Csillag K. Szakonyi Z. Fülöp F. Tetrahedron: Asymmetry 2013; 24: 553

6a Yao Y. Xu L. Mini. Rev. Org. Chem. 2016; 13: 184
6b Marcelli T. Hiemstra H. Synthesis 2010; 1229
6c Jarvo ER. Miller SJ. Tetrahedron 2002; 58: 2481
6d Wang T. Han X. Zhong F. Yao W. Lu Y. Acc. Chem. Res. 2016; 49: 1369
6e Xu L.-W. Lu Y. Org. Biomol. Chem. 2008; 6: 2047

7a El Alami MS. I. El Amrani MA. Agbossou-Niedercorn F. Suisse I. Mortreux A. Chem. Eur. J. 2015; 21: 1398
7b Brown HC. Ramachandran PV. Acc. Chem. Res. 1992; 25: 16

8a Groselj U. Curr. Org. Chem. 2015; 19: 2048
8b Chuo TH. Boobalan R. Chen C. ChemistrySelect 2016; 1: 2174
8c Ričko S. Svete J. Štefane B. Perdih A. Golobič A. Meden A. Grošelj U. Adv. Synth. Catal. 2016; 358: 3786

9a Bui T. Borregan M. Barbas CF. III. J. Org. Chem. 2009; 74: 8935
9b Chadha AW. B. Y. L. Davis W. J. Org. Chem. 1993; 58: 844

10 Brzezinski LJ. Rafel S. Leahy JW. J. Am. Chem. Soc. 1997; 119: 4317

11a Lou L.-L. Zhang J. Du H. Zhao B. Li S. Yu W. Yu K. Liu S. Catal. Today 2016; 264: 109
11b Machajewski TD. Wong CH. Angew. Chem. Int. Ed. 2000; 39: 1352

12a Lou S. Taoka BM. Ting A. Schaus SE. J. Am. Chem. Soc. 2005; 127: 11256
12b Cui XY. Duan HX. Zhang Y. Wang YQ. Chem. Asian J. 2016; 11: 3118

13a Chen X. Dang T.-TT. Facchini PJ. Phytochemistry 2015; 111: 7
13b Segal MS. Goldstein MM. Attinger EO. Chest J. 1957; 32: 305

14a Salehi P. Dabiri M. Kozehgary G. Baghbanzadeh M. Tetrahedron: Asymmetry 2009; 20: 2609 ; Highlighted in Synfacts 2010, 203
14b Dabiri M. Salehi P. Kozehgary G. Heydari S. Heydari A. Esfandyari M. Tetrahedron: Asymmetry 2008; 19: 1970

15 Aga MA. Kumar B. Rouf A. Shah BA. Taneja SC. Tetrahedron Lett. 2014; 55: 2639
16 Huang H. Zong H. Bian G. Song L. J. Org. Chem. 2015; 80: 12614
17 Yue H. Huang H. Bian G. Zong H. Li F. Song L. Tetrahedron: Asymmetry 2014; 25: 170
18 Yu J. Long J. Yang Y. Wu W. Xue P. Chung LW. Dong X.-Q. Zhang X. Org. Lett. 2017; 19: 690
19 Zhang C.-H. Yan S.-J. Pan S.-Q. Huang R. Lin J. Bull. Korean Chem. Soc. 2010; 31: 869

Supplementary Material

Supporting Information

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

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