A Michael route to acetals and thioacetals: Preparation of acetals (thioacetals) of 2-sulfonylacetaldehyde from alkynyl and other unsaturated aryl sulfones

Synthesis

Volumn , Issue 12, 1996, Pages 1481-1484

  Cossu, Sergio ^a   De Lucchi, Ottorino ^a   Fabris, Fabrizio ^a   Ballini, Roberto ^b   Bosica, Giovanna ^a  

^a CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

^b Via S Agostino 1   (Italy)

Author keywords

1,2 bis(phenylsulfonyl)ethylene; acetals; acetyl sulfones; ethynyl tolylsulfone; nucleophilic addition

Indexed keywords

ACETAL;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030476569     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4406     Document Type: Article

References (21)

1. De Lucchi, O.; Cossu, S. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. Ed.; Wiley & Sons: New York, 1995; p 4033, and references cited therein. Chen, Z.; Trudell, M. L. Synth. Commun. 1994, 24, 3149.
2. De Lucchi, O.; Cossu, S. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. Ed.; Wiley & Sons: New York, 1995; p 4033, and references cited therein. Chen, Z.; Trudell, M. L. Synth. Commun. 1994, 24, 3149.
3. De Lucchi, O.; Pasquato, L. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. Ed.; Wiley & Sons; New York, 1995, p 547 and references cited therein.
4. Kharash, N.; Assony, S. J. J. Am. Chem. Soc. 1955, 77, 3390.
5. Capozzi, G.; Modena, G.; Pasquato, L. In The Chemistry of Sulphenic Acid and their Derivatives; Patai, S. Ed.; Wiley & Sons: New York, 1990, Chap 10, p 403, and references cited therein. Rasteikiene, L.; Greiciute, D.; Lin'kova, M. G.; Knunyants, I. L. Russ. Chem. Rev. 1977, 46, 548. Kühle, E. Synthesis 1971, 563. Amiel, Y. J. Org. Chem. 1971, 36, 3697, and references cited therein. Caló, V.; Modena, G.; Scorrano, G. J. Org. Chem. 1969, 34, 2020. Montanari, F. Gazz. Chim. Ital. 1956, 86, 415.
6. Capozzi, G.; Modena, G.; Pasquato, L. In The Chemistry of Sulphenic Acid and their Derivatives; Patai, S. Ed.; Wiley & Sons: New York, 1990, Chap 10, p 403, and references cited therein. Rasteikiene, L.; Greiciute, D.; Lin'kova, M. G.; Knunyants, I. L. Russ. Chem. Rev. 1977, 46, 548. Kühle, E. Synthesis 1971, 563. Amiel, Y. J. Org. Chem. 1971, 36, 3697, and references cited therein. Caló, V.; Modena, G.; Scorrano, G. J. Org. Chem. 1969, 34, 2020. Montanari, F. Gazz. Chim. Ital. 1956, 86, 415.
7. Capozzi, G.; Modena, G.; Pasquato, L. In The Chemistry of Sulphenic Acid and their Derivatives; Patai, S. Ed.; Wiley & Sons: New York, 1990, Chap 10, p 403, and references cited therein. Rasteikiene, L.; Greiciute, D.; Lin'kova, M. G.; Knunyants, I. L. Russ. Chem. Rev. 1977, 46, 548. Kühle, E. Synthesis 1971, 563. Amiel, Y. J. Org. Chem. 1971, 36, 3697, and references cited therein. Caló, V.; Modena, G.; Scorrano, G. J. Org. Chem. 1969, 34, 2020. Montanari, F. Gazz. Chim. Ital. 1956, 86, 415.
8. Capozzi, G.; Modena, G.; Pasquato, L. In The Chemistry of Sulphenic Acid and their Derivatives; Patai, S. Ed.; Wiley & Sons: New York, 1990, Chap 10, p 403, and references cited therein. Rasteikiene, L.; Greiciute, D.; Lin'kova, M. G.; Knunyants, I. L. Russ. Chem. Rev. 1977, 46, 548. Kühle, E. Synthesis 1971, 563. Amiel, Y. J. Org. Chem. 1971, 36, 3697, and references cited therein. Caló, V.; Modena, G.; Scorrano, G. J. Org. Chem. 1969, 34, 2020. Montanari, F. Gazz. Chim. Ital. 1956, 86, 415.
9. Capozzi, G.; Modena, G.; Pasquato, L. In The Chemistry of Sulphenic Acid and their Derivatives; Patai, S. Ed.; Wiley & Sons: New York, 1990, Chap 10, p 403, and references cited therein. Rasteikiene, L.; Greiciute, D.; Lin'kova, M. G.; Knunyants, I. L. Russ. Chem. Rev. 1977, 46, 548. Kühle, E. Synthesis 1971, 563. Amiel, Y. J. Org. Chem. 1971, 36, 3697, and references cited therein. Caló, V.; Modena, G.; Scorrano, G. J. Org. Chem. 1969, 34, 2020. Montanari, F. Gazz. Chim. Ital. 1956, 86, 415.
10. Capozzi, G.; Modena, G.; Pasquato, L. In The Chemistry of Sulphenic Acid and their Derivatives; Patai, S. Ed.; Wiley & Sons: New York, 1990, Chap 10, p 403, and references cited therein. Rasteikiene, L.; Greiciute, D.; Lin'kova, M. G.; Knunyants, I. L. Russ. Chem. Rev. 1977, 46, 548. Kühle, E. Synthesis 1971, 563. Amiel, Y. J. Org. Chem. 1971, 36, 3697, and references cited therein. Caló, V.; Modena, G.; Scorrano, G. J. Org. Chem. 1969, 34, 2020. Montanari, F. Gazz. Chim. Ital. 1956, 86, 415.
11. Schaumann, E. In Perspectives in the Organic Chemistry of Sulphur; Zwanenburg, B.; Klunder, A. J. H. Eds.; Elsevier: Amsterdam, 1987; p 251. De Lucchi, O.; Buso, M.; Modena, G. Tetrahedron Lett. 1987, 28, 107. De Lucchi, O.; Lucchini, V.; Marchioro, C.; Modena, G. Tetrahedron Lett. 1985, 26, 4539.
12. Schaumann, E. In Perspectives in the Organic Chemistry of Sulphur; Zwanenburg, B.; Klunder, A. J. H. Eds.; Elsevier: Amsterdam, 1987; p 251. De Lucchi, O.; Buso, M.; Modena, G. Tetrahedron Lett. 1987, 28, 107. De Lucchi, O.; Lucchini, V.; Marchioro, C.; Modena, G. Tetrahedron Lett. 1985, 26, 4539.
13. Schaumann, E. In Perspectives in the Organic Chemistry of Sulphur; Zwanenburg, B.; Klunder, A. J. H. Eds.; Elsevier: Amsterdam, 1987; p 251. De Lucchi, O.; Buso, M.; Modena, G. Tetrahedron Lett. 1987, 28, 107. De Lucchi, O.; Lucchini, V.; Marchioro, C.; Modena, G. Tetrahedron Lett. 1985, 26, 4539.
14. See for example: Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715. Kodomari, M.; Saitoh, G.; Yoshitomi, S. Bull. Chem. Soc. Jpn. 1991, 64, 3485. Sharaf, S. M.; El-Sadany, S.; Hamed, E. A.; Youssef, A.-H. A. Can. J. Chem. 1991, 69, 1445. Guillot, C.; Maignan, C. Tetrahedron Lett. 1991, 32, 4907. Selling, H. A. Tetrahedron 1975, 31, 2387.
15. See for example: Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715. Kodomari, M.; Saitoh, G.; Yoshitomi, S. Bull. Chem. Soc. Jpn. 1991, 64, 3485. Sharaf, S. M.; El-Sadany, S.; Hamed, E. A.; Youssef, A.-H. A. Can. J. Chem. 1991, 69, 1445. Guillot, C.; Maignan, C. Tetrahedron Lett. 1991, 32, 4907. Selling, H. A. Tetrahedron 1975, 31, 2387.
16. See for example: Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715. Kodomari, M.; Saitoh, G.; Yoshitomi, S. Bull. Chem. Soc. Jpn. 1991, 64, 3485. Sharaf, S. M.; El-Sadany, S.; Hamed, E. A.; Youssef, A.-H. A. Can. J. Chem. 1991, 69, 1445. Guillot, C.; Maignan, C. Tetrahedron Lett. 1991, 32, 4907. Selling, H. A. Tetrahedron 1975, 31, 2387.
17. See for example: Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715. Kodomari, M.; Saitoh, G.; Yoshitomi, S. Bull. Chem. Soc. Jpn. 1991, 64, 3485. Sharaf, S. M.; El-Sadany, S.; Hamed, E. A.; Youssef, A.-H. A. Can. J. Chem. 1991, 69, 1445. Guillot, C.; Maignan, C. Tetrahedron Lett. 1991, 32, 4907. Selling, H. A. Tetrahedron 1975, 31, 2387.
18. See for example: Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715. Kodomari, M.; Saitoh, G.; Yoshitomi, S. Bull. Chem. Soc. Jpn. 1991, 64, 3485. Sharaf, S. M.; El-Sadany, S.; Hamed, E. A.; Youssef, A.-H. A. Can. J. Chem. 1991, 69, 1445. Guillot, C.; Maignan, C. Tetrahedron Lett. 1991, 32, 4907. Selling, H. A. Tetrahedron 1975, 31, 2387.
19. Lee, J. W.; Oh, D. Y. Synlett 1990, 290.
20. Diamines add to two moles of alkyne regardless of the ratio of reagents under the same reaction conditions.
21. Meek, J. S.; Fowler, J. S. J. Org. Chem. 1968, 985.