Highly chemo- and stereoselective Fe-catalyzed alkenylation of organomanganese reagents

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1773-1776

  Cahiez, Gérard ^a   Marquais, Sophie ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029970234     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00116-5     Document Type: Article

References (18)

1. Organomanganese Reagents Part XXXI. These results have been presented at the OMCOS-8 Symposium in Santa Barbara, California, USA on August 8, 1995.
2. Kumada, M. Pure Appl. Chem. 1980, 52, 669-679. Tamao, K.; Kumada, M. in The Chemistry of the Metal-Carbon Bond, Chap. 4, p.819, 1987, F.R. Hartley Ed., Wiley & Son, New York. Negishi, E. Acc. Chem. Res. 1982, 15, 340-348. Erdik, E. Tetrahedron 1992, 48, 9577-9648. Knochel, P. and Singer, R.D. Chem. Rev. 1993, 93, 2117-2188. Stille, J.K. Angew. Chem. 1986, 98, 505-519. Kalini, V.N. Synthesis 1992, 413-432. Suzuki, A. Pure Appl Chem. 1985, 57, 1749-1758.
3. Kumada, M. Pure Appl. Chem. 1980, 52, 669-679. Tamao, K.; Kumada, M. in The Chemistry of the Metal-Carbon Bond, Chap. 4, p.819, 1987, F.R. Hartley Ed., Wiley & Son, New York. Negishi, E. Acc. Chem. Res. 1982, 15, 340-348. Erdik, E. Tetrahedron 1992, 48, 9577-9648. Knochel, P. and Singer, R.D. Chem. Rev. 1993, 93, 2117-2188. Stille, J.K. Angew. Chem. 1986, 98, 505-519. Kalini, V.N. Synthesis 1992, 413-432. Suzuki, A. Pure Appl Chem. 1985, 57, 1749-1758.
4. Kumada, M. Pure Appl. Chem. 1980, 52, 669-679. Tamao, K.; Kumada, M. in The Chemistry of the Metal-Carbon Bond, Chap. 4, p.819, 1987, F.R. Hartley Ed., Wiley & Son, New York. Negishi, E. Acc. Chem. Res. 1982, 15, 340-348. Erdik, E. Tetrahedron 1992, 48, 9577-9648. Knochel, P. and Singer, R.D. Chem. Rev. 1993, 93, 2117-2188. Stille, J.K. Angew. Chem. 1986, 98, 505-519. Kalini, V.N. Synthesis 1992, 413-432. Suzuki, A. Pure Appl Chem. 1985, 57, 1749-1758.
5. Kumada, M. Pure Appl. Chem. 1980, 52, 669-679. Tamao, K.; Kumada, M. in The Chemistry of the Metal-Carbon Bond, Chap. 4, p.819, 1987, F.R. Hartley Ed., Wiley & Son, New York. Negishi, E. Acc. Chem. Res. 1982, 15, 340-348. Erdik, E. Tetrahedron 1992, 48, 9577-9648. Knochel, P. and Singer, R.D. Chem. Rev. 1993, 93, 2117-2188. Stille, J.K. Angew. Chem. 1986, 98, 505-519. Kalini, V.N. Synthesis 1992, 413-432. Suzuki, A. Pure Appl Chem. 1985, 57, 1749-1758.
6. Kumada, M. Pure Appl. Chem. 1980, 52, 669-679. Tamao, K.; Kumada, M. in The Chemistry of the Metal-Carbon Bond, Chap. 4, p.819, 1987, F.R. Hartley Ed., Wiley & Son, New York. Negishi, E. Acc. Chem. Res. 1982, 15, 340-348. Erdik, E. Tetrahedron 1992, 48, 9577-9648. Knochel, P. and Singer, R.D. Chem. Rev. 1993, 93, 2117-2188. Stille, J.K. Angew. Chem. 1986, 98, 505-519. Kalini, V.N. Synthesis 1992, 413-432. Suzuki, A. Pure Appl Chem. 1985, 57, 1749-1758.
7. Kumada, M. Pure Appl. Chem. 1980, 52, 669-679. Tamao, K.; Kumada, M. in The Chemistry of the Metal-Carbon Bond, Chap. 4, p.819, 1987, F.R. Hartley Ed., Wiley & Son, New York. Negishi, E. Acc. Chem. Res. 1982, 15, 340-348. Erdik, E. Tetrahedron 1992, 48, 9577-9648. Knochel, P. and Singer, R.D. Chem. Rev. 1993, 93, 2117-2188. Stille, J.K. Angew. Chem. 1986, 98, 505-519. Kalini, V.N. Synthesis 1992, 413-432. Suzuki, A. Pure Appl Chem. 1985, 57, 1749-1758.
8. Kumada, M. Pure Appl. Chem. 1980, 52, 669-679. Tamao, K.; Kumada, M. in The Chemistry of the Metal-Carbon Bond, Chap. 4, p.819, 1987, F.R. Hartley Ed., Wiley & Son, New York. Negishi, E. Acc. Chem. Res. 1982, 15, 340-348. Erdik, E. Tetrahedron 1992, 48, 9577-9648. Knochel, P. and Singer, R.D. Chem. Rev. 1993, 93, 2117-2188. Stille, J.K. Angew. Chem. 1986, 98, 505-519. Kalini, V.N. Synthesis 1992, 413-432. Suzuki, A. Pure Appl Chem. 1985, 57, 1749-1758.
9. Kumada, M. Pure Appl. Chem. 1980, 52, 669-679. Tamao, K.; Kumada, M. in The Chemistry of the Metal-Carbon Bond, Chap. 4, p.819, 1987, F.R. Hartley Ed., Wiley & Son, New York. Negishi, E. Acc. Chem. Res. 1982, 15, 340-348. Erdik, E. Tetrahedron 1992, 48, 9577-9648. Knochel, P. and Singer, R.D. Chem. Rev. 1993, 93, 2117-2188. Stille, J.K. Angew. Chem. 1986, 98, 505-519. Kalini, V.N. Synthesis 1992, 413-432. Suzuki, A. Pure Appl Chem. 1985, 57, 1749-1758.
10. a/ Tamura, M. and Kochi, J.K. J. Am. Chem. Soc. 1971, 93, 1487-1489.
11. b/ Neumann, S.M. and Kochi, J.K. J. Org. Chem. 1975, 40, 599-606.
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14. Cahiez, G. and Marquais, S. Synlett 1993, 45-47.
15. 7 (70 mmoles) in 80 ml of THF are added, at room temperature, 50 ml of distilled NMP, 3% Fe(acac)3 (1.5 mmoles) then a solution of alkenyl halide (50 mmoles) in 10 ml of THF. The reaction mixture was stirred for 1 to 2 hours at room temperature then hydrolyzed with 80 ml of aqueous hydrochloric acid (1M) at -10°C. After classical work up (extraction with ether), the desired product was isolated by distillation.
16. For the preparation of RMnCl see: Cahiez, G. and Alami, M. Tetrahedron 1989, 45, 4163-4176. Cahiez, G. Butyl Manganese Chloride and Related Reagents in Encyclopedia of Reagents for Organic Synthesis, L. Paquette Ed., Wiley, Chichester 1995, in press,
17. For the preparation of RMnCl see: Cahiez, G. and Alami, M. Tetrahedron 1989, 45, 4163-4176. Cahiez, G. Butyl Manganese Chloride and Related Reagents in Encyclopedia of Reagents for Organic Synthesis, L. Paquette Ed., Wiley, Chichester 1995, in press,
18. b/ Cahiez, G. Manganese (II) Chloride in Encyclopedia of Reagents for Organic Synthesis, L. Paquette Ed., Wiley, Chichester 1995, in press.