A Mild Method for Indium(III)-Catalyzed 1,4-Hydrosilylation of α,β-Enone Esters with Triethylsilane and Trifluoroacetic Acid

Ping Xing; Wei Zang; Zuo-gang Huang; Yue-xiong Zhan; Chuan-jun Zhu; Biao Jiang

doi:10.1055/s-0031-1290448

Synlett, Table of Contents

Synlett 2012; 23(15): 2269-2273
DOI: 10.1055/s-0031-1290448

letter

A Mild Method for Indium(III)-Catalyzed 1,4-Hydrosilylation of α,β-Enone Esters with Triethylsilane and Trifluoroacetic Acid

Authors

Ping Xing

^aKey Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China, Fax: +86(21)64166128 Email: jiangb@sioc.ac.cn
Wei Zang

^aKey Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China, Fax: +86(21)64166128 Email: jiangb@sioc.ac.cn
Zuo-gang Huang

^bShanghai Advanced Research Institute, Chinese Academy of Sciences, 99 Haike Road, Shanghai 201210, P. R. of China
Yue-xiong Zhan

^aKey Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China, Fax: +86(21)64166128 Email: jiangb@sioc.ac.cn
Chuan-jun Zhu

^bShanghai Advanced Research Institute, Chinese Academy of Sciences, 99 Haike Road, Shanghai 201210, P. R. of China
Biao Jiang*

^aKey Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China, Fax: +86(21)64166128 Email: jiangb@sioc.ac.cn

^bShanghai Advanced Research Institute, Chinese Academy of Sciences, 99 Haike Road, Shanghai 201210, P. R. of China

Abstract

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Abstract

A chemo- and stereoselective 1,4-hydrosilylation of α,β-enone esters was developed using triethylsilane and trifluoroacetic acid under indium chloride catalysis.

Key words

1,4-hydrosilylation - α,β-enone ester - indium chloride - triethylsilane - silyl enol ether

Full Text

References

References and Notes
1 Olah GA, Arvanaghi M, Ohannesian L. Synthesis 1986; 770

2a Mayr H, Dogan B. Tetrahedron Lett. 1997; 38: 1013
2b West CT, Donnelly SJ, Kooistra DA, Doyle MP. J. Org. Chem. 1973; 38: 2675

3 Olah GA, Wang Q, Prakash GK. S. Synlett 1992; 647
4 Chang Y.-H, Pinnick HW. J. Org. Chem. 1978; 43: 374

5a Yato M, Homma K, Ishida A. Heterocycles 1995; 41: 17
5b Bhattacharyya S. J. Org. Chem. 1998; 63: 7101

6 Li Z, Deng G, Li Y.-C. Synlett 2008; 3053
7 Yoshii E, Koizumi T, Hayashi I, Hiroi Y. Chem. Pharm. Bull. 1977; 25: 1468
8 Keinan E, Greenspoon N. J. Am. Chem. Soc. 1986; 108: 7314
9 Mori A, Fujita A, Hiroshi K, Nishihara Y, Hiyama T. Tetrahedron 1999; 55: 4573

10a Hog DT, Oestreich M. Eur. J. Org. Chem. 2009; 5047
10b Lee O.-Y, Law K.-L, Yang D. Org. Lett. 2009; 11: 3302
10c Fernandes AC, Romao C. Tetrahedron Lett. 2005; 46: 8881
10d Tobisu M, Nkamura R, Kita Y, Chatani N. Bull. Korean Chem. Soc. 2010; 31: 582

11a Anada M, Tanaka M, Suzuki K, Nambu H, Hashimoto S. Chem. Pharm. Bull. 2006; 54: 1622
11b Blackwell JM, Morrison DJ, Piers WE. Tetrahedron 2002; 58: 8247
11c Mori A, Kato T. Synlett 2002; 1167

12a Hoffman RV, Johnson MC, Okonya JF. J. Org. Chem. 1997; 62: 2458
12b Okonya JF, Johnson MC, Hoffman RV. J. Org. Chem. 1998; 63: 6409

13a Other indium salts like InF₃, InBr₃, InI₃, and In(OTf)₃ resulted in no reaction or complex mixtures.
13b Using TiCl₄ or BF₃·OEt₂ instead of InCl₃ resulted in only 12–23% yields.

14 Other silanes like Ph₂SiH₂, (MeO)₃SiH, (EtO)₃SiH, and Cl₃SiH resulted in no reaction or complex mixtures.
15 For a Rh-catalyzed 1,4-hydrosilylation of α,β-enone to generate Z/E intermediates, see: Anada M, Tanaka M, Washio T, Yamawaki M, Abe T, Hashimoto S. Org. Lett. 2007; 9: 4559

16a Seneci P, Leger I, Souchet M, Nadler G. Tetrahedron 1997; 53: 17097
16b Grison C, Petek S, Coutrot P. Synlett 2005; 331

Supplementary Material

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