Tris(pentafluorophenyl)borane-Catalyzed Synthesis of N-Benzyl Pyrrolidines

Pabbaraja Srihari; Srinivasa Rao Yaragorla; Debjit Basu; Srivari Chandrasekhar

doi:10.1055/s-2006-942501

SHORTPAPER

Tris(pentafluorophenyl)borane-Catalyzed Synthesis of N-Benzyl Pyrrolidines

Pabbaraja Srihari*, Srinivasa Rao Yaragorla, Debjit Basu, Srivari Chandrasekhar
Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: srihari@iict.res.in;

Abstract

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Abstract

1,3-Dipolar cycloaddition of in situ generated azomethine ylides to electron deficient olefins catalyzed tris(pentafluorophenyl)borane is described.

Key words

cycloaddition - dipole - pyrrolidine - azomethine ylide - heterocycles

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References

<A NAME="RZ07106SS-1A">1a</A> Tomioka K. Nakajima M. Litaka Y. Koga K. Tetrahedron Lett. 1988, 29: 573

<A NAME="RZ07106SS-1B">1b</A> Tomioka K. Nakajima M. Koga K. Tetrahedron Lett. 1990, 31: 1741

<A NAME="RZ07106SS-1C">1c</A> Nakajima M. Tomioka K. Litaka Y. Koga K. Tetrahedron 1993, 49: 10793

<A NAME="RZ07106SS-1D">1d</A> Elbein AD. Annu. Rev. Biochem. 1987, 56: 497

<A NAME="RZ07106SS-1E">1e</A> Winchester B. Fleet GWJ. Glycobiology 1992, 2: 199

<A NAME="RZ07106SS-2A">2a</A> Ghosh AK. Bilcer G. Schiltz G. Synthesis 2001, 2203

<A NAME="RZ07106SS-2B">2b</A> List B. Castello C. Synlett 2001, 1687

<A NAME="RZ07106SS-2C">2c</A> Harwood LM. Vickers RJ. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products Padwa A. Pearson WH. Wiley & Sons; New York: 2002. p.169-252

<A NAME="RZ07106SS-2D">2d</A> Kraus GA. Nagy JO. Tetrahedron 1985, 41: 3537

<A NAME="RZ07106SS-2E">2e</A> Wang C.-L. Ripka WC. Congalone PN. Tetrahedron Lett. 1984, 25: 4613

<A NAME="RZ07106SS-2F">2f</A> Garner P. Ho WB. Shin H. J. Am. Chem. Soc. 1992, 114: 2767

<A NAME="RZ07106SS-3A">3a</A> Najera C. Sansano JM. Curr. Org. Chem. 2003, 7: 1105

<A NAME="RZ07106SS-3B">3b</A> Dogan O. Oner I. Ulku D. Arici C. Tetrahedron: Asymmetry 2002, 13: 2099

<A NAME="RZ07106SS-3C">3c</A> Kanemasa S. Synlett 2002, 1371

<A NAME="RZ07106SS-4A">4a</A> Grigg R. Kemp J. J. Chem. Soc., Chem. Commun. 1978, 109

<A NAME="RZ07106SS-4B">4b</A> Joucla M. Hamelin J. Tetrahedron Lett. 1978, 19: 2885

<A NAME="RZ07106SS-4C">4c</A> Tsuge O. Ueno K. Oe K. Chem. Lett. 1979, 1407

<A NAME="RZ07106SS-4D">4d</A> Grigg R. Bull. Soc. Chim. Belg. 1984, 93: 593

<A NAME="RZ07106SS-4E">4e</A> Tsuge O. Ueno K. Heterocycles 1982, 19: 1411

<A NAME="RZ07106SS-4F">4f</A> Tsuge O. Kanemasa S. Yorozu K. Ueno K. Chem. Lett. 1985, 1601

<A NAME="RZ07106SS-4G">4g</A> Tsuge O. Ueno K. Kanemasa S. Yorozu K. Bull. Chem. Soc. Jpn. 1986, 59: 1809

<A NAME="RZ07106SS-5A">5a</A> Komatsu M. Okada H. Yokoi S. Minakata SS. Tetrahedron Lett. 2003, 44: 1603

<A NAME="RZ07106SS-5B">5b</A> Wee AGH. J. Chem. Soc., Perkin Trans. 1 1989, 1363

<A NAME="RZ07106SS-5C">5c</A> Vedejs E. West FG. Chem. Rev. 1986, 86: 941

<A NAME="RZ07106SS-5D">5d</A> Padwa A. Fryxell GE. Gasdaska JR. Venkatramanan MK. Wong GSK. J. Org. Chem. 1989, 54: 644

<A NAME="RZ07106SS-5E">5e</A> Grigg R. Kemp J. J. Chem. Soc., Chem. Commun. 1978, 109

<A NAME="RZ07106SS-5F">5f</A> Tsuge O. Kanemasa S. Ohe M. Takenaka S. Chem. Lett. 1986, 973

<A NAME="RZ07106SS-5G">5g</A> Tsuge O. Kanemasa M. Hatada A. Matsuda K. Bull. Chem. Soc. Jpn. 1986, 59: 2537

<A NAME="RZ07106SS-6A">6a</A> Huisgen R. Scheer W. Huber H. Tetrahedron Lett. 1966, 7: 397

<A NAME="RZ07106SS-6B">6b</A> Huisgen R. Scheer W. Huber H. J. Am. Chem. Soc. 1967, 89: 1753

<A NAME="RZ07106SS-6C">6c</A> Garner P. Dogan O. J. Org. Chem. 1994, 59: 4

<A NAME="RZ07106SS-6D">6d</A> Deshong P. Kell DA. Tetrahedron Lett. 1986, 27: 3979

<A NAME="RZ07106SS-7A">7a</A> Grigg R. Thornton-Pett M. Xu J. Xu L.-H. Tetrahedron 1999, 55: 13841

<A NAME="RZ07106SS-7B">7b</A> Alcaide B. Almendros P. Alonso JM. Aly MF. J. Org. Chem. 2001, 66: 1351

<A NAME="RZ07106SS-7C">7c</A> Garner P. Kaniskan HU. Tetrahedron Lett. 2005, 46: 5181

<A NAME="RZ07106SS-7D">7d</A> Najera C. Sansano JM. Angew. Chem. Int. Ed. 2005, 44: 6272

<A NAME="RZ07106SS-8A">8a</A> Dogan O. Koyuncu H. Kaniskan U. Turk. J. Chem. 2001, 25: 365

<A NAME="RZ07106SS-8B">8b</A> Suga H. Inoue K. Inoue S. Kakehi A. J. Am. Chem. Soc. 2002, 124: 14836

<A NAME="RZ07106SS-8C">8c</A> Husinec S. Savic V. Tetrahedron: Asymmetry 2005, 16: 2047

<A NAME="RZ07106SS-8D">8d</A> Bowman RK. Johnson SJ. J. Org. Chem. 2004, 69: 8537

<A NAME="RZ07106SS-9">9</A> Chandrasekhar S. Raji Reddy Ch. Nagendra Babu B. J. Org. Chem. 2002, 67: 9080

<A NAME="RZ07106SS-10">10</A> Chandrasekhar S. Raji Reddy Ch. Nagendra Babu B. Chandrasekhar G. Tetrahedron Lett. 2002, 43: 3801

<A NAME="RZ07106SS-11">11</A> Chandrasekhar S. Nagendra Babu B. Chandrasekhar G. Vijeender K. Reddy KV. Tetrahedron Lett. 2004, 45: 5497

For our recent publications on this catalyst, see:

<A NAME="RZ07106SS-12A">12a</A> Chandrasekhar S. Chandrashekar G. Srinivasa Reddy M. Srihari P. Org. Biomol. Chem. 2006, 4: 1650

<A NAME="RZ07106SS-12B">12b</A> Chandrasekhar S. Srinivasa Rao Y. Ramakrishna Reddy N. Synlett 2005, 1471

<A NAME="RZ07106SS-12C">12c</A> Chandrasekhar S. Babu BN. Chandrashekar G. eEROS Electronic Encyclopedia of Organic Reagents for Organic Synthesis J. Wiley; New York: 2005. p.120 ; and references therein

For compound preparation, see:

<A NAME="RZ07106SS-13A">13a</A> Hosomi A. Sakata Y. Sakurai H. Chem. Lett. 1984, 1117

<A NAME="RZ07106SS-13B">13b</A> Padwa A. Dent W. J. Org. Chem. 1987, 52: 235

<A NAME="RZ07106SS-14">14</A> No attempts were made to study the mechanism in detail.

<A NAME="RZ07106SS-15">15</A> Wee AGH. J. Chem. Soc., Perkin Trans. 1 1989, 1363