Cobalt(I)-Catalyzed Stereoselective Olefination of Alkylzinc Reagents with Aldehydes

Jin-Xian Wang; Ying Fu; Yulai Hu; Kehu Wang

doi:10.1055/s-2003-40509

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 X Linkedin Weibo

Download PDF

Synthesis 2003(10): 1506-1510
DOI: 10.1055/s-2003-40509

PAPER

Cobalt(I)-Catalyzed Stereoselective Olefination of Alkylzinc Reagents with Aldehydes

Jin-Xian Wang*^a,b, Ying Fu^a, Yulai Hu^a, Kehu Wang^a
^a Institute of Chemistry, Department of Chemistry, Northwest Normal University, Lanzhou 730070, P. R. China.
Fax: +86(931)7768159; e-Mail: Wangjx@nwnu.edu.cn;
^b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.

Further Information

Publication History

Received 17 February 2003
Publication Date:
08 July 2003 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

The efficient olefination from organozinc reagents with aldehydes is exploited in a new synthesis of aryl and alkyl olefins.

Key words

alkenation - zinc - aldehydes - cobalt - organometallic reagents - alkenes

References

1a Maryanoff BE. Reitz AB. Chem. Res. 1989, 89: 863

Crossref Google Scholar
1b Maercher A. Org. React. 1965, 14: 270

Crossref Google Scholar
1c Johnson AW. Ylid Chemistry Academic Press; New York: 1966.

Crossref Google Scholar
1d Becker KB. Synthesis 1983, 341

Crossref Google Scholar
1e Burton DJ. Yang ZY. Qiu W. Chem. Rev. 1996, 52: 1641

Crossref Google Scholar
1f Vedejs E. Marth CF. J. Am. Chem. Soc. 1988, 110: 3948

Crossref Google Scholar
2 Mc Murry JE. Fleming MP. J. Am. Chem. Soc. 1974, 96: 4708

Crossref PubMed Google Scholar
3 Engman L. J. Org. Chem. 1984, 49: 3559

Google Scholar
4 Vedejs E. Dolphin JM. Stolle WT. J. Am. Chem. Soc. 1979, 101: 249

Crossref Google Scholar
5 Katritzky AR. Tymoshenko DO. Belyakov SA. J. Org. Chem. 1999, 64: 3332

Crossref Google Scholar
6a Kabalka GW. Maddox JT. Bogas E. J. Org. Chem. 1994, 59: 5530

Crossref Google Scholar
6b Kabalka GW. Wu Z. Ju Y. Tetrahedron 2001, 57: 1663

Crossref Google Scholar
7a Soai K. Niwa S. Chem. Rev. 1992, 92: 833

Crossref Google Scholar
7b Noyori R. Kitamura M. Angew. Chem., Int. Ed. Engl. 1991, 30: 34

Crossref Google Scholar
8a Dosa PI. Fu GC. J. Am. Chem. Soc. 1998, 120: 445

Article in Thieme Connect Google Scholar
8b Lutz C. Jones P. Knochel P. Synthesis 1999, 312

Article in Thieme Connect Google Scholar
9 Hu Y. Yu J. Yang S. Wang J.-X. Yin Y. Synlett 1998, 1213

Article in Thieme Connect Google Scholar
10 Hu Y. Wang J.-X. Li W. Chem. Lett. 2001, 174

Crossref Google Scholar
11 Wang J.-X. Fu Y. Hu Y. Angew. Chem. Int. Ed. 2002, 41: 2757

Crossref Google Scholar
12 Gerrard AF. Djerassi C. J. Am. Chem. Soc. 1969, 91: 6808

Crossref Google Scholar
13 Meyers AI. Ford ME. J. Org. Chem. 1976, 41: 1735

Google Scholar
14 Citter A. Minisci F. Arnoldi A. Pagano R. Parravicini A. Porta O. J. Chem. Soc., Perkin Trans. 2 1978, 519

Google Scholar
15 Ramart-Lucas M. Amagat P. Bull. Soc. Chim. Fr. 1932, 965

Google Scholar
16 Cowan DO. Baum AA. J. Am. Chem. Soc. 1971, 93: 1153

Crossref Google Scholar
17 Himmele W, Bott K, and Bronstert K. inventors; Eur. Pat. Appl. EP314003. ; Chem. Abstr. 1989, 111, P194267w
18 Hu Y. Yu J. Yang S. Wang J.-X. Yin Y. Synth. Commun. 1999, 29: 1157

Google Scholar
19 Mori A. Suguro M. Synlett 2001, 845

Article in Thieme Connect Google Scholar
20 Seebach D. Schaefer H. Schmidt B. Schreiber M. Angew. Chem., Int. Ed. Engl. 1992, 31: 1587

Crossref Google Scholar
21 Pelter A. Buss D. Colcough E. Singaram B. Tetrahedron 1993, 49: 7077

Crossref Google Scholar
22 Miyaura N. Yamada K. Suginome H. Suzuki A. J. Am. Chem. Soc. 1985, 107: 972

Crossref Google Scholar
23 Rudenko MG. Soblev YuP. Neftekhimiya 1996, 6: 312

Google Scholar