Isolation of the Quinone Mono O,S-Acetal Intermediates of the Aromatic Pummerer-Type Rearrangement of p-Sulfinytpnenols with 1-Ethoxyvinyl Esters

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 13-14, 1997, Pages 1529-1531

  Kita, Yasuyuki ^a   Takeda, Yoshifumi ^a   Matsugi, Masato ^a   Iio, Kiyosei ^a   Gotanda, Kentoku ^a   Murata, Kenji ^a   Akai, Shuji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Acetals; Pummerer rearrangement; Quinones; Rearrangements; Sulfur

Indexed keywords

EID: 0030799835     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199715291     Document Type: Article

References (20)

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2. Reviews: a) S. Oae, T. Numata, T. Yoshimura in The Chemistry of the Sulphonium Group (Eds.: C. J. M. Stirling, S. Patai), Wiley, New York, 1981, p. 571; b) O. D. Lucchi, U. Miotti, G. Modena, Organic Reactions, Vol. 40, Wiley, New York, 1991, chapter 3; c) D. S. Grierson, H.-P. Husson in Comprehensive Organic Synthesis, Vol. 6 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 909; d) Y. Kita, N. Shibata, Synlett 1996, 289-296. Recently published examples: e) A. Hedhli, A. Baklouti, A. Cambon, Tetrahedron Lett. 1994, 37, 6877-6878; f) A. Arnone, P. Bravo, M. Frigerio, G. Salani, F. Viani, Tetrahedron 1994, 50, 13485-13492.
3. Reviews: a) S. Oae, T. Numata, T. Yoshimura in The Chemistry of the Sulphonium Group (Eds.: C. J. M. Stirling, S. Patai), Wiley, New York, 1981, p. 571; b) O. D. Lucchi, U. Miotti, G. Modena, Organic Reactions, Vol. 40, Wiley, New York, 1991, chapter 3; c) D. S. Grierson, H.-P. Husson in Comprehensive Organic Synthesis, Vol. 6 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 909; d) Y. Kita, N. Shibata, Synlett 1996, 289-296. Recently published examples: e) A. Hedhli, A. Baklouti, A. Cambon, Tetrahedron Lett. 1994, 37, 6877-6878; f) A. Arnone, P. Bravo, M. Frigerio, G. Salani, F. Viani, Tetrahedron 1994, 50, 13485-13492.
4. Reviews: a) S. Oae, T. Numata, T. Yoshimura in The Chemistry of the Sulphonium Group (Eds.: C. J. M. Stirling, S. Patai), Wiley, New York, 1981, p. 571; b) O. D. Lucchi, U. Miotti, G. Modena, Organic Reactions, Vol. 40, Wiley, New York, 1991, chapter 3; c) D. S. Grierson, H.-P. Husson in Comprehensive Organic Synthesis, Vol. 6 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 909; d) Y. Kita, N. Shibata, Synlett 1996, 289-296. Recently published examples: e) A. Hedhli, A. Baklouti, A. Cambon, Tetrahedron Lett. 1994, 37, 6877-6878; f) A. Arnone, P. Bravo, M. Frigerio, G. Salani, F. Viani, Tetrahedron 1994, 50, 13485-13492.
5. Reviews: a) S. Oae, T. Numata, T. Yoshimura in The Chemistry of the Sulphonium Group (Eds.: C. J. M. Stirling, S. Patai), Wiley, New York, 1981, p. 571; b) O. D. Lucchi, U. Miotti, G. Modena, Organic Reactions, Vol. 40, Wiley, New York, 1991, chapter 3; c) D. S. Grierson, H.-P. Husson in Comprehensive Organic Synthesis, Vol. 6 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 909; d) Y. Kita, N. Shibata, Synlett 1996, 289-296. Recently published examples: e) A. Hedhli, A. Baklouti, A. Cambon, Tetrahedron Lett. 1994, 37, 6877-6878; f) A. Arnone, P. Bravo, M. Frigerio, G. Salani, F. Viani, Tetrahedron 1994, 50, 13485-13492.
6. Reviews: a) S. Oae, T. Numata, T. Yoshimura in The Chemistry of the Sulphonium Group (Eds.: C. J. M. Stirling, S. Patai), Wiley, New York, 1981, p. 571; b) O. D. Lucchi, U. Miotti, G. Modena, Organic Reactions, Vol. 40, Wiley, New York, 1991, chapter 3; c) D. S. Grierson, H.-P. Husson in Comprehensive Organic Synthesis, Vol. 6 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 909; d) Y. Kita, N. Shibata, Synlett 1996, 289-296. Recently published examples: e) A. Hedhli, A. Baklouti, A. Cambon, Tetrahedron Lett. 1994, 37, 6877-6878; f) A. Arnone, P. Bravo, M. Frigerio, G. Salani, F. Viani, Tetrahedron 1994, 50, 13485-13492.
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14. We have elucidated a highly enantioselective Pummerer-type reaction of chiral, nonracemic aliphatic sulfoxides using O-silylated ketene acetals [1d], although the enantiomeric excesses for the reported asymmetric Pummerer reaction induced by acid anhydrides were low [1]. This method was efficiently applied to the asymmetric Pummerer-type cyclization of chiral, nonracemic sulfoxides and to the biomimetic conversion of Arnstein tripeptide analogs into optically active cis β-lactams. This synthesis resembles penicillin biosynthesis [9a]. Similar highly enantioselective Pummerer-type reactions of chiral, nonracemic aliphatic sulfoxides induced by a variety of 1-ethoxyvinyl esters including 2a,b also gave α-acyloxy sulfides [9b,c].
15. a) Y. Kita, N. Shibata, N. Kawano, T. Tohjo, C. Fujimori, H. Ohishi, J. Am. Chem. Soc. 1994, 116, 5116-5121;
16. b) Y. Kita, N. Shibata, N. Kawano, S. Fukui, C. Fujimori, Tetrahedron Lett. 1994, 38, 3575-3576;
17. c) N. Shibata, M. Matsugi, N. Kawano, S. Fukui, C. Fujimori, K. Gotanda, K. Murata, Y. Kita, Tetrahedron: Asymmetry 1997, 8, 303-310.
18. Y. Kita, H. Maeda, K. Omori, T. Okuno, Y. Tamura, J. Chem. Soc. Perkin Trans. 1 1993, 2999-3005, and references therein.
19. Although the preparation of p-quinone mono O,O-acetal compounds has been widely explored, most of the methods that have been applied thus far are based on the oxidation of phenol or dihydroquinone derivatives: a) Y. Tamura, T. Yakura, J. Haruta, Y. Kita, J. Org. Chem. 1987, 52, 3927-3930; b) E. C. L. Gautier, N. J. Lewis, A. McKillop, R. J. K. Tayler, Synth. Commun. 1994, 24, 2989-3008, and references therein.
20. Although the preparation of p-quinone mono O,O-acetal compounds has been widely explored, most of the methods that have been applied thus far are based on the oxidation of phenol or dihydroquinone derivatives: a) Y. Tamura, T. Yakura, J. Haruta, Y. Kita, J. Org. Chem. 1987, 52, 3927-3930; b) E. C. L. Gautier, N. J. Lewis, A. McKillop, R. J. K. Tayler, Synth. Commun. 1994, 24, 2989-3008, and references therein.