Novel Regio- and Stereoselective
Synthesis of Functionalized 3-Spiropyrrolidines and 3-Spiropyrrolizidines
Using the Baylis-Hillman Adducts Derived from
Nitroolefins

Manickam Bakthadoss; Nagappan Sivakumar

doi:10.1055/s-0028-1088206

RSS-Feed abonnieren

Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.

https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml

Teilen / Bookmarken

Facebook X Linkedin Weibo

PDF herunterladen

Synlett 2009(6): 1014-1018
DOI: 10.1055/s-0028-1088206

LETTER

Novel Regio- and Stereoselective Synthesis of Functionalized 3-Spiropyrrolidines and 3-Spiropyrrolizidines Using the Baylis-Hillman Adducts Derived from Nitroolefins

Manickam Bakthadoss*, Nagappan Sivakumar
Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600025, Tamilnadu, India
Fax: +91(44)22352494; e-Mail: bhakthadoss@yahoo.com;

Weitere Informationen

Publikationsverlauf

Received 2 October 2008
Publikationsdatum:
16. März 2009 (online)

Abstract
Volltext
Referenzen

Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

A facile regio- and stereoselective synthesis of functionalized 3-spiropyrrolidines and 3-spiropyrrolizidines using the Baylis-Hillman adducts derived from nitroolefins via intermolecular [3+2] cycloaddition reaction is reported.

Key words

Baylis-Hillman reaction - intermolecular [3+2] cycloaddition - azomethine ylides - 1,3-dipolar cycloaddition - spiro compounds

References and Notes

1 Basavaiah D. Rao KV. Reddy RJ. Chem. Soc. Rev. 2007, 36: 1581

Crossref PubMed Google Scholar
2 Basavaiah D. Rao AJ. Satyanarayana T. Chem. Rev. 2003, 103: 811

Crossref PubMed Google Scholar
3 Singh V. Batra S. Tetrahedron 2008, 64: 4511

Crossref Google Scholar
4 Basavaiah D. Rao PD. Hyma S. Tetrahedron 1996, 52: 8001

Crossref Google Scholar
5 Ciganek E. In Organic Reactions Vol. 51: Paquette LA. Wiley; New York: 1997. p.201-350

Google Scholar
6 Jossang A. Jossang P. Hadi HA. Sevenet T. Bodo B. J. Org. Chem. 1991, 56: 6527

Crossref Google Scholar
7 James MNG. Williams GJB. Can. J. Chem. 1972, 50: 2407

Crossref Google Scholar
8 Elderfield RC. Gilman RE. Phytochemistry 1972, 11: 339

Crossref Google Scholar
9 Cui CB. Kakeya H. Okada G. Onose R. Osada H. J. Antibiot. 1996, 49: 527

Crossref Google Scholar
10a De Amici M. De Michelli C. Sani VM. Tetrahedron 1990, 46: 1975

Google Scholar
10b Early WG. Oh T. Overman LE. Tetrahedron Lett. 1988, 29: 3785

Google Scholar
10c Kozikowski AP. Acc. Chem. Res. 1984, 17: 410

Google Scholar
10d Ban Y. Taga N. Oishi T. Chem. Pharm. Bull. 1976, 24: 736

Google Scholar
10e Van Tamlen EE. Yardley JP. Miyano M. Hinshaw WB. J. Am. Chem. Soc. 1969, 26: 7333

Google Scholar
10f Howe RK. Shelton BR. J. Org. Chem. 1990, 55: 4603

Google Scholar
10g Cohen VL, and Kleinman EE. inventors; WO 24, 398. ; Chem. Abstr. 1995, 122, 20667j
10h Ban Y. Seto M. Oishi T. Chem. Pharm. Bull. 1975, 23: 2605

Google Scholar
10i Ban Y. Taga N. Oishi T. Tetrahedron Lett. 1974, 15: 187

Google Scholar
10j Caroll WA. Grieco PA. J. Am. Chem. Soc. 1993, 115: 1164

Google Scholar
11 Ding K. Lu Y. Nikolovska-Coleska Z. Wang G. Qiu S. Shangary S. Gao W. Qin D. Stuckey J. Krajewski K. Roller PP. Wang S. J. Med. Chem. 2006, 49: 3432

Crossref PubMed Google Scholar
12 Hilton ST. Ho TCT. Pljevaljcic G. Jones K. Org. Lett. 2000, 2: 2639

Crossref Google Scholar
13 Zeni G. Larock RC. Chem. Rev. 2006, 106: 4644

Crossref PubMed Google Scholar
14 Basavaiah D. Roy S. Org. Lett. 2008, 10: 1819

Crossref Google Scholar
15 Savitha G. Niveditha SK. Muralidharan D. Perumal PT. Tetrahedron Lett. 2007, 48: 2943

Crossref Google Scholar
16a Muthusamy S. Gunanathan C. Babu SA. Tetrahedron Lett. 2001, 42: 523

Google Scholar
16b Shanmugam P. Viswambharan B. Madhavan S. Org. Lett. 2007, 9: 4095

Google Scholar
17 Coldham I. Hufton R. Chem. Rev. 2005, 105: 2765

Crossref PubMed Google Scholar
18a Pandey G. Banerjee P. Gadre SR. Chem. Rev. 2006, 106: 4484

Google Scholar
18b Petrovskaia O. Taylor BM. Hauze DB. Carroll PJ. Joullie MM. J. Org. Chem. 2001, 66: 7666

Google Scholar
18c Fokas D. Ryan WJ. Casebier DS. Coffen DL. Tetrahedron Lett. 1998, 39: 2235

Google Scholar
18d Ghandi M. Rezaei SJT. Yari A. Taheri A. Tetrahedron Lett. 2008, 49: 5899

Google Scholar
18e Panja SK. Karmakar P. Chakraborty J. Ghosh T. Bandyopadhyay C. Tetrahedron Lett. 2008, 49: 4397

Google Scholar
19a Baylis AB, and Hillman MED. inventors; DE 2155113. ; Chem. Abstr. 1972, 77, 34174q
19b Rastogi N. Namboothiri INN. Cojocaru M. Tetrahedron Lett. 2004, 45: 4745

Google Scholar
20a Webber P. Krische MJ. J. Org. Chem. 2008, 73: 9379

Google Scholar
20b Alcaide B. Almendros P. Aragoncillo C. J. Org. Chem. 2001, 66: 1612

Google Scholar
20c Zhong W. Zhao Y. Su W. Tetrahedron 2008, 64: 5491

Google Scholar
21 Bakthadoss M. Sivakumar N. Sivakumar G. Murugan G. Tetrahedron Lett. 2008, 49: 820

Crossref Google Scholar
22 Basavaiah D. Bakthadoss M. Pandiaraju S. Chem. Commun. 1998, 1639

Crossref Google Scholar
23 Basavaiah D. Bakthadoss M. Jayapal Reddy G. Synthesis 2001, 919

Artikel in Thieme Connect Google Scholar
24a Basavaiah D. Bakthadoss M. Jayapal Reddy G. Synth. Commun. 2002, 32: 689

Google Scholar
24b Bakthadoss M. Murugan G. Synth. Commun. 2008, 38: 3406

Google Scholar

25

The X-ray crystal structure data of 6a and 7d have been deposited at the Cambrigde Crystallographic Data Centre and allocated the deposition numbers CCDC 676397 (6a), and CCDC 676668 (7d). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.