Efficient Lewis Base-Catalyzed Conjugate Addition of Azide Ion to Cyclic Enones in Water

Li-Wen Xu; Chun-Gu Xia; Jing-Wei Li; Shao-Lin Zhou

doi:10.1055/s-2003-42043

LETTER

Efficient Lewis Base-Catalyzed Conjugate Addition of Azide Ion to Cyclic Enones in Water

Li-Wen Xu, Chun-Gu Xia*, Jing-Wei Li, Shao-Lin Zhou
State Key Laboratory of Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou, 730000, P. R. China
Fax: 86(931)8277088; e-Mail: cgxia@ns.lzb.ac.cn;

Abstract

All articles of this category

Abstract

The first, environmental benign, highly efficient conjugate addition of azide ion to cyclic enones catalyzed by simple Lewis base in the green solvent, water, are described.

Key words

Lewis bases - conjugate addition - enones - sodium azide - water

Full Text

References

1a The Organic Chemistry of β-Lactams George GI. VCH Publishers; New York: 1993.

1b Cardill G. Tomasini C. Chem. Soc. Rev. 1996, 117

1c Juaristi E. Lopez-Ruiz H. Curr. Med. Chem. 1999, 6: 983

1d Seebach D. Matthews JL. J. Chem. Soc., Chem. Commun. 1997, 2015

1e Drury WJ. Ferraris D. Cox C. Young B. Leckta T. J. Am. Chem. Soc. 1998, 120: 11006

1f Hagiwara E. Fujii A. Sodeoka M. J. Am. Chem. Soc. 1998, 120: 2474

1g Abele S. Seebach D. Eur. J. Org. Chem. 2000, 6: 1

2a Arend M. Westermann B. Risch N. Angew. Chem. Int. Ed. 1998, 37: 1044

2b Sibi MP. Shay JJ. Liu M. Jasperse CP. J. Am. Chem. Soc. 1998, 120: 6615

3a Ishitani H. Ueno M. Kobayashi S. J. Am. Chem. Soc. 2000, 122: 8180

3b Zhuang W. Hazell RG. Jorgensen KA. Chem. Commun. 2001, 1240

3c Bartoli G. Bosco M. Marcantoni E. Pertrini M. Sambri L. Torregiani E. J. Org. Chem. 2001, 66: 9052

3d Nakama K. Seki S. Tetrahedron Lett. 2002, 43: 829

4a Gaunt MJ. Spencer JB. Org. Lett. 2001, 3: 25

4b Kobayashi S. Kakumoto K. Sugiura M. Org. Lett. 2002, 4: 1319

4c Wabnitz TC. Yu JQ. Spencer JB. Synlett 2003, 1070

4d Wabnitz TC. Spencer JB. Org. Lett. 2003, 5: 2141

4e Srivastava N. Banik BK. J. Org. Chem. 2003, 68: 2109

5 Wabnitz TC. Spencer JB. Tetrahedron Lett. 2002, 43: 3891

6a Chung BY. Park YS. Cho IS. Hyun BC. Bull. Korean Chem. Soc. 1988, 9: 269

6b Magnus P. Lacour J. Evans PA. Roe MB. Hulme C. J. Am. Chem. Soc. 1996, 118: 3406

6c Enantioselective Synthesis of β-Amino Acids Juaristi E. Wiley-VCH; New York: 1997.

7 Biffin MEC. Miller SJ. Paul DB. In The Chemistry of the Azido Group Patai S. Interscience Publishers; London: 1971. p.57-190

8 Lakshmipathi P. Rao AVR. Tetrahedron Lett. 1997, 38: 2551

9 Guerin DJ. Horstmann TE. Miller SJ. Org. Lett. 1999, 1: 1107

10a Myers JK. Jacobsen EN. J. Am. Chem. Soc. 1999, 121: 8959

10b Horstmann TE. Guerin DJ. Miller SJ. Angew. Chem. Int. Ed. 2000, 39: 3635

Selected new references:

11a Lewis Acids Inorganic Synthesis Yamamoto H. Wiley-VCH; Weinheim: 2000.

11b Denmark SE. Fan Y. J. Am. Chem. Soc. 2003, 125: 7825

11c Labrie P. Synlett 2003, 279

11d Szmigielski R. Danikiewicz W. Synlett 2003, 372

11e Chen FX. Feng XM. Qin B. Zhang GL. Jiang YZ. Synlett 2003, 558

11f Peyronneau M. Roques N. Mazieres S. Le Roux C. Synlett 2003, 631

12a Nagano Y. Orita A. Otera J. Adv. Synth. Catal. 2003, 345: 643

12b Bartoli G. Bosco M. Dalpozzo R. Marcantoni E. Massaccesi M. Rinaldi S. Sambri L. Synlett 2003, 39

12c Kobayashi S. Manabe AK. Acc. Chem. Res. 2002, 35: 209 ; and references cited therein

13a Keh CCK. Wei C. Li CJ. J. Am. Chem. Soc. 2003, 125: 4062

13b Doncaster JR. Ryan H. Whitehead RC. Synlett 2003, 651

13c Iimura S. Nobutou D. Manabe K. Kobayashi S. Chem. Commun. 2003, 1644

13d Li CJ. Acc. Chem. Res. 2002, 35: 533

13e Lindström UM. Chem. Rev. 2002, 102: 2751 ; and references cited therein

14a Denmark SE. Wynm T. J. Am. Chem. Soc. 2001, 123: 6199

14b Stewart IC. Bergman RG. Toste FD. J. Am. Chem. Soc. 2003, 125: 8696

15

All these known products were identified by GC-MS (Agilent 6890N GC/5973N MS, HP-5MS).