Iron(II)-catalyzed intramolecular aminochlorination of alkenes

Chemical Communications

Volumn , Issue 4, 2000, Pages 287-288

  Bach, Thorsten ^a   Schlummer, Björn ^a   Harms, Klaus ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AZIDE; FERROUS ION; OXAZOLIDINONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHLORINATION; CONFORMATION; ELECTRON TRANSPORT; NONHUMAN; STEREOCHEMISTRY;

EID: 0034696305     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a909009f     Document Type: Article

References (18)

1. Review on the asymmetric synthesis of aziridines: H. M. I. Osborn and J. Sweeney, Tetrahedron: Asymmetry, 1997, 8, 1693.
2. Some selected examples: D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Org. Chem., 1991, 56, 6744; K. J. O'Connor, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543; J. U. Jeong, B. Tao, I. Sagasser, H. Henniges and K. B. Sharpless, J. Am. Chem. Soc., 1998, 120, 6844.
3. Some selected examples: D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Org. Chem., 1991, 56, 6744; K. J. O'Connor, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543; J. U. Jeong, B. Tao, I. Sagasser, H. Henniges and K. B. Sharpless, J. Am. Chem. Soc., 1998, 120, 6844.
4. Some selected examples: D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Org. Chem., 1991, 56, 6744; K. J. O'Connor, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543; J. U. Jeong, B. Tao, I. Sagasser, H. Henniges and K. B. Sharpless, J. Am. Chem. Soc., 1998, 120, 6844.
5. Some selected examples: D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Org. Chem., 1991, 56, 6744; K. J. O'Connor, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543; J. U. Jeong, B. Tao, I. Sagasser, H. Henniges and K. B. Sharpless, J. Am. Chem. Soc., 1998, 120, 6844.
6. Some selected examples: D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Org. Chem., 1991, 56, 6744; K. J. O'Connor, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543; J. U. Jeong, B. Tao, I. Sagasser, H. Henniges and K. B. Sharpless, J. Am. Chem. Soc., 1998, 120, 6844.
7. Some selected examples: D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Org. Chem., 1991, 56, 6744; K. J. O'Connor, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543; J. U. Jeong, B. Tao, I. Sagasser, H. Henniges and K. B. Sharpless, J. Am. Chem. Soc., 1998, 120, 6844.
8. Some selected examples: D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Org. Chem., 1991, 56, 6744; K. J. O'Connor, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543; J. U. Jeong, B. Tao, I. Sagasser, H. Henniges and K. B. Sharpless, J. Am. Chem. Soc., 1998, 120, 6844.
9. Review: P. Müller, in Advances in Catalytic Processes Vol. 2, Asymmetric Catalysis, ed. M. P Doyle, JAI, , Greenwich, 1997, pp. 131-151.
10. T. Bach and C. Körber, Tetrahedron Lett., 1998, 39, 5015; T. Bach and C. Körber, Eur. J. Org. Chem., 1999, 1033.
11. T. Bach and C. Körber, Tetrahedron Lett., 1998, 39, 5015; T. Bach and C. Körber, Eur. J. Org. Chem., 1999, 1033.
12. (a) S. C. Bergmeier and D. M. Stanchina, Tetrahedron Lett., 1995, 36, 4533;
13. (b) S. C. Bergmeier and D. M. Stanchina, J. Org. Chem., 1997, 62, 4449.
14. 3: P. Yuan, P. Plourde, M. R. Shoemaker, C. L. Moore and D. E. Hansen, J. Org. Chem., 1995, 60, 5360. CAUTION! Alkoxycarbonyl azides are potential explosives. Appropriate safety protection and utmost care are required while handling these compounds.
15. 2 (13 mg, 0.10 mmol) was added in one portion to the stirred solution. The formerly colorless reaction mixture turned yellow and nitrogen started to evolve. The solution was allowed to warm to room temperature and was stirred for another 20 h. It was then dissolved in EtOAc (20 ml) and washed with water (2 × 20 ml) and brine (20 ml). The organic layer was dried over MgSO4 and the solvent was removed in vacua. The brown residue was purified by chromatography on silica using pentane-tert-butyl methyl ether (2:8) as the eluent. A mixture of 2a and 3a was obtained as colorless crystals (156 mg, 72%, dr = 91:9). The analytical data were in agreement with the literature values (ref. 5).
16. 2 = 0.1310, R = 0.0459 [I > 2σ(I)]. CCDC 182/1523.
17. Reviews: A. G. Fallis and I. M. Brinza, Tetrahedron, 1997, 53, 17543; D. Savoia, in Houben-Weyl Methoden der Organischen Chemie, 4th edn., ed. G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, Thieme, Stuttgart, 1996, vol. E21, pp. 5265-5273.
18. Reviews: A. G. Fallis and I. M. Brinza, Tetrahedron, 1997, 53, 17543; D. Savoia, in Houben-Weyl Methoden der Organischen Chemie, 4th edn., ed. G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, Thieme, Stuttgart, 1996, vol. E21, pp. 5265-5273.