Thioorthoesters in the activated Pictet-Spengler cyclization. Synthesis of 1-thiosubstituted tetrahydroisoquinolines and carbon-carbon bond formation via sulfonyl iminium ions generated from N,S-sulfonyl acetals

Tetrahedron Letters

Volumn 44, Issue 32, 2003, Pages 6137-6140

  Silveira, Claudio C ^a   Bernardi, Carmem R ^a   Braga, Antonio L ^a   Kaufman, Teodoro S ^b  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b Universidad Nacional de Rosario   (Argentina)

Author keywords

1 substituted tetrahydroisoquinolines; Activated Pictet Spengler; Sulfonyl iminium ions; Thioorthoesters

Indexed keywords

ACETAL DERIVATIVE; CARBON; ESTER DERIVATIVE; IMINE; TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 0037967857     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01452-7     Document Type: Article

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45. The Lewis acid-promoted carbon-carbon bond formation employing (S,S), (Se,Se) and mixed (O,S) and (O,Se) acetals has been studied. See, for example: (a) Hunter, R.; Michael, J. P.; Walter, D. S. Tetrahedron Lett. 1994, 35, 5481-5484; (b) Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1990, 55, 6116-6121; (c) Braga, A. L.; Dornelles, L.; Silveira, C. C.; Wessjohann, L. A. Synthesis 1999, 562-564; (d) Hermans, B.; Hevesi, L. J. Org. Chem. 1995, 60, 6141-6147; (e) Silveira, C. C.; Larghi, E. L. J. Braz. Chem. Soc. 1998, 9, 327-340 and references cited therein.
46. The Lewis acid-promoted carbon-carbon bond formation employing (S,S), (Se,Se) and mixed (O,S) and (O,Se) acetals has been studied. See, for example: (a) Hunter, R.; Michael, J. P.; Walter, D. S. Tetrahedron Lett. 1994, 35, 5481-5484; (b) Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1990, 55, 6116-6121; (c) Braga, A. L.; Dornelles, L.; Silveira, C. C.; Wessjohann, L. A. Synthesis 1999, 562-564; (d) Hermans, B.; Hevesi, L. J. Org. Chem. 1995, 60, 6141-6147; (e) Silveira, C. C.; Larghi, E. L. J. Braz. Chem. Soc. 1998, 9, 327-340 and references cited therein.
47. The Lewis acid-promoted carbon-carbon bond formation employing (S,S), (Se,Se) and mixed (O,S) and (O,Se) acetals has been studied. See, for example: (a) Hunter, R.; Michael, J. P.; Walter, D. S. Tetrahedron Lett. 1994, 35, 5481-5484; (b) Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1990, 55, 6116-6121; (c) Braga, A. L.; Dornelles, L.; Silveira, C. C.; Wessjohann, L. A. Synthesis 1999, 562-564; (d) Hermans, B.; Hevesi, L. J. Org. Chem. 1995, 60, 6141-6147; (e) Silveira, C. C.; Larghi, E. L. J. Braz. Chem. Soc. 1998, 9, 327-340 and references cited therein.
48. The Lewis acid-promoted carbon-carbon bond formation employing (S,S), (Se,Se) and mixed (O,S) and (O,Se) acetals has been studied. See, for example: (a) Hunter, R.; Michael, J. P.; Walter, D. S. Tetrahedron Lett. 1994, 35, 5481-5484; (b) Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1990, 55, 6116-6121; (c) Braga, A. L.; Dornelles, L.; Silveira, C. C.; Wessjohann, L. A. Synthesis 1999, 562-564; (d) Hermans, B.; Hevesi, L. J. Org. Chem. 1995, 60, 6141-6147; (e) Silveira, C. C.; Larghi, E. L. J. Braz. Chem. Soc. 1998, 9, 327-340 and references cited therein.