A Novel One-Pot Stereoselective Synthesis of N-[(E)-Homocinnamyl] Amides

Wanli Chen; Xian Huang; Hongwei Zhou

doi:10.1055/s-2004-822369

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook Linkedin Weibo

Download PDF

Synthesis 2004(10): 1573-1576
DOI: 10.1055/s-2004-822369

PAPER

A Novel One-Pot Stereoselective Synthesis of N-[(E)-Homocinnamyl] Amides

Wanli Chen^a, Xian Huang*^a,b, Hongwei Zhou^a
^a Department of Chemistry, Zhejiang University (Campus Xixi), Hangzhou 310028, P. R. China
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China
Fax: +86(571)88807077; e-Mail: huangx@mail.hz.zj.cn;

Further Information

Publication History

Received 23 February 2004
Publication Date:
18 May 2004 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

N-[(E)-Homocinnamyl] amides were stereoselectively synthesized by the reaction of the methylenecyclopropanes (MCPs) with nitriles under acidic conditions in moderate yields in a one-pot manner.

Key words

Ritter reaction - methylenecyclopropanes - nitriles - stereoselectively - N-homocinnamyl amides

Reference

1a Petragnani N. Stefani HA. Valduga CJ. Tetrahedron 2001, 57: 1411

Crossref Search in Google Scholar
1b Angela LM. Brent LP. Edward WH. David AD. Norton PP. Herschel JRW. Michael RA. J. Org. Chem. 1994, 59: 2092

Crossref Search in Google Scholar
1c Gawley RE. Chemburkar S. Tetrahedron Lett. 1986, 27: 2071

Crossref Search in Google Scholar
2 Gawley RE. Chemburkar SR. Heterocycles 1989, 29: 1283

Search in Google Scholar
3 Synthesis of MCPs: Brandi A. Goti A. Chem. Rev. 1998, 98: 589

Crossref PubMed Search in Google Scholar
Recent reviews of MCPs:
4a Brandi A. Cicchi S. Cordero FM. Goti A. Chem. Rev. 2003, 103: 1213

Search in Google Scholar
4b Nakamura I. Yamamoto Y. Adv. Synth. Catal. 2002, 2: 111

Search in Google Scholar
4c Yamago S. Nakamura E. Org. React. 2002, 61: 1

Search in Google Scholar
4d Nakamura E. Yamago S. Acc. Chem. Res. 2002, 35: 867

Search in Google Scholar
4e Yamago S. Takeichi A. Nakamura E. Synthesis 1996, 1380
4f Binger P. Buch HM. Top. Curr. Chem. 1987, 135: 77

Search in Google Scholar
4g Ohta T. Takaya H. In Comprehensive Organic Synthesis Vol. 5: Trost BM. Pergamon; Oxford: 1991. p.1185

Search in Google Scholar
5a Krimer LI. Cota D. Org. React. 1969, 17: 213

Crossref Search in Google Scholar
5b Bishop R. In Comprehensive Organic Synthesis Vol. 6: Trost BM. Fleming I. Winterfeldt E. Pergamon; Oxford: 1991. p.261

Crossref Search in Google Scholar
5c Reddy KL. Tetrahedron Lett. 2003, 44: 1453

Crossref Search in Google Scholar
5d Ma SM. Hao XS. Huang X. Chem. Commun. 2003, 1082

Crossref
6a Huang X. Zhou HW. Org. Lett. 2002, 4: 4419

Crossref Search in Google Scholar
6b Zhou HW. Huang X. Chen WL. Synlett 2003, 2080

Crossref
6c Huang X. Chen WL. Zhou HW. Synlett 2004, 329

Crossref
6d Huang X. Zhou HW. Chen WL. J. Org. Chem. 2004, 69: 839

Crossref Search in Google Scholar
7 Siriwardana AI. Nakamura I. Yamamoto Y. Tetrahedron Lett. 2003, 44: 985

Crossref Search in Google Scholar
For stable cyclopropylcarbinyl cations:
8a Klunder AJH. Zwanenburg B. In Houben-Weyl Vol. E17c: de Meijere A. Thieme; Stuttgart, Germany: 1977. p.2419

Search in Google Scholar
8b March J. Advanced Organic Chemistry 4th ed.: Wiley; New York: 1992. p.169 ; and references cited therein

Search in Google Scholar
9 Utimoto K. Tamura M. Sisido K. Tetrahedron 1973, 14: 1169

Search in Google Scholar