Copper(II) triflate-mediated addition reaction of α-sulfurated alkylstannanes to imines: Facile synthesis of vicinal-amino sulfides

Chemistry Letters

Volumn 33, Issue 8, 2004, Pages 962-963

  Kagoshima, Hirotaka ^a   Takahashi, Naoshi ^a  

^a IBARAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DECARBOXYLASE; COPPER COMPLEX; IMINE; SULFIDE; TIN DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; QUANTUM YIELD; REACTION ANALYSIS;

EID: 8844233499     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.962     Document Type: Article

References (24)

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13. For other synthetic methods for vicinal-amino sulfides: a) R. K. Dieter and M. Tokles, J. Am. Chem. Soc., 109, 2040 (1987). b) G. S. Poindexter, D. A. Owens, P. L. Dolan, and E. Woo, J. Org. Chem., 57, 6257 (1992). c) B. S. Orlek, Synlett, 1996, 477. d) R. Siedlecka and J. Skarzewski, Synlett, 1996, 757. e) H. Ishibashi, M. Uegaki, and M. Sakai, Synlett, 1997, 915.
14. For other synthetic methods for vicinal-amino sulfides: a) R. K. Dieter and M. Tokles, J. Am. Chem. Soc., 109, 2040 (1987). b) G. S. Poindexter, D. A. Owens, P. L. Dolan, and E. Woo, J. Org. Chem., 57, 6257 (1992). c) B. S. Orlek, Synlett, 1996, 477. d) R. Siedlecka and J. Skarzewski, Synlett, 1996, 757. e) H. Ishibashi, M. Uegaki, and M. Sakai, Synlett, 1997, 915.
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21. These stannanes were prepared by modifications of the literature procedures for analogous α-sulfurated alkylstannanes: K. Narasaka, N. Arai, and T. Okauchi, Bull. Chem. Soc. Jpn., 66, 2995 (1993).
22. 2 was reduced to 0.5 equiv.
23. α-Sulfurated alkylstannanes are easily oxidized with metallic oxidants. See, Ref. 6.
24. 3. After a usual work up, the crude product was purified by TLC (AcOEt:hexane = 1:30) to give the corresponding product 3a (18 mg, 56%, diastereomer ratio = 49:51).