Diastereotopic group selective intramolecular cycloadditions of sulfenic acids to 1,4-dienes

Organic and Biomolecular Chemistry

Volumn 2, Issue 2, 2004, Pages 151-153

  Grainger, Richard S ^a   Tisselli, Patrizia ^a   Steed, Jonathan W ^a  

^a KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ALKYLATION; ETHERS; HYDROLYSIS; ISOMERS; ORGANIC ACIDS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

DIASTEREOTOPIC GROUP; INTRAMOLECULAR CYCLOADDITIONS;

ADDITION REACTIONS;

EID: 1642524965     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b314176d     Document Type: Article

References (37)

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5. Representative examples involving diastereotopic alkene and alkyne groups: (a) S. F. Martin, S. K. Davidsen and T. A. Puckette, J. Org. Chem., 1987, 52, 1962; (b) S. F. Martin and C. L. Campbell, J. Org. Chem., 1988, 53, 3184; (c) P. Wipf and Y. Kim, Tetrahedron Lett., 1992, 33, 5477; (d) P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848; (e) D. Bland, D. J. Hart and S. Lacoutiere, Tetrahedron, 1997, 53, 8871; (f) D. Bland, G. Chambournier, V. Dragan and D. J. Hart, Tetrahedron, 1999, 55, 8953; (g) H. Fujioka, S. Kitagaki, N. Ohno, H. Kitagawa, Y. Kita and K. Matsumoto, Tetrahedron: Asymmetry, 1994, 5, 333; (h) M. C. Carreño, M. P. González, M. Ribagorda and K. N. Houk, J. Org. Chem., 1998, 63, 3687; (i) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; (J) M. Suginome, Y. Yamamoto, K. Fujii and Y. Ito, J. Am. Chem. Soc., 1995, 117, 9608; (k) D. P. Curran, S. J. Geib and C.-H. Lin, Tetrahedron: Asymmetry, 1994, 5, 199; (l) D. P. Curran, C.-H. Lin, N. DeMello and J. Junggebauer, J. Am. Chem. Soc., 1998, 120, 342; (m) F. Villar, T. Kolly-Kovac, O. Equey and P. Renaud, Chem. Eur. J., 2003, 9, 1566; (n) T. M. Nguyen, R. J. Seifert, D. R. Mowrey and D. Lee, Org. Lett., 2002, 4, 3959; (o) T. Ishikawa, K. Shimizu, H. Ishii, S. Ikeda and S. Saito, J. Org. Chem., 2001, 66, 3834; (p) K. Ohmori, Y. Hachisu, T. Suzuki and K. Suzuki, Tetrahedron Lett., 2002, 43, 1031; (q) Y.-i. Fukuda, H. Sasaki, M. Shindo and K. Shishido, Tetrahedron Lett., 2002, 43, 2047; (r) P. A. Evans, J. Cui and G. P. Buffone, Angew. Chem., Int. Ed., 2003, 42, 1734.
6. Representative examples involving diastereotopic alkene and alkyne groups: (a) S. F. Martin, S. K. Davidsen and T. A. Puckette, J. Org. Chem., 1987, 52, 1962; (b) S. F. Martin and C. L. Campbell, J. Org. Chem., 1988, 53, 3184; (c) P. Wipf and Y. Kim, Tetrahedron Lett., 1992, 33, 5477; (d) P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848; (e) D. Bland, D. J. Hart and S. Lacoutiere, Tetrahedron, 1997, 53, 8871; (f) D. Bland, G. Chambournier, V. Dragan and D. J. Hart, Tetrahedron, 1999, 55, 8953; (g) H. Fujioka, S. Kitagaki, N. Ohno, H. Kitagawa, Y. Kita and K. Matsumoto, Tetrahedron: Asymmetry, 1994, 5, 333; (h) M. C. Carreño, M. P. González, M. Ribagorda and K. N. Houk, J. Org. Chem., 1998, 63, 3687; (i) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; (J) M. Suginome, Y. Yamamoto, K. Fujii and Y. Ito, J. Am. Chem. Soc., 1995, 117, 9608; (k) D. P. Curran, S. J. Geib and C.-H. Lin, Tetrahedron: Asymmetry, 1994, 5, 199; (l) D. P. Curran, C.-H. Lin, N. DeMello and J. Junggebauer, J. Am. Chem. Soc., 1998, 120, 342; (m) F. Villar, T. Kolly-Kovac, O. Equey and P. Renaud, Chem. Eur. J., 2003, 9, 1566; (n) T. M. Nguyen, R. J. Seifert, D. R. Mowrey and D. Lee, Org. Lett., 2002, 4, 3959; (o) T. Ishikawa, K. Shimizu, H. Ishii, S. Ikeda and S. Saito, J. Org. Chem., 2001, 66, 3834; (p) K. Ohmori, Y. Hachisu, T. Suzuki and K. Suzuki, Tetrahedron Lett., 2002, 43, 1031; (q) Y.-i. Fukuda, H. Sasaki, M. Shindo and K. Shishido, Tetrahedron Lett., 2002, 43, 2047; (r) P. A. Evans, J. Cui and G. P. Buffone, Angew. Chem., Int. Ed., 2003, 42, 1734.
7. Representative examples involving diastereotopic alkene and alkyne groups: (a) S. F. Martin, S. K. Davidsen and T. A. Puckette, J. Org. Chem., 1987, 52, 1962; (b) S. F. Martin and C. L. Campbell, J. Org. Chem., 1988, 53, 3184; (c) P. Wipf and Y. Kim, Tetrahedron Lett., 1992, 33, 5477; (d) P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848; (e) D. Bland, D. J. Hart and S. Lacoutiere, Tetrahedron, 1997, 53, 8871; (f) D. Bland, G. Chambournier, V. Dragan and D. J. Hart, Tetrahedron, 1999, 55, 8953; (g) H. Fujioka, S. Kitagaki, N. Ohno, H. Kitagawa, Y. Kita and K. Matsumoto, Tetrahedron: Asymmetry, 1994, 5, 333; (h) M. C. Carreño, M. P. González, M. Ribagorda and K. N. Houk, J. Org. Chem., 1998, 63, 3687; (i) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; (J) M. Suginome, Y. Yamamoto, K. Fujii and Y. Ito, J. Am. Chem. Soc., 1995, 117, 9608; (k) D. P. Curran, S. J. Geib and C.-H. Lin, Tetrahedron: Asymmetry, 1994, 5, 199; (l) D. P. Curran, C.-H. Lin, N. DeMello and J. Junggebauer, J. Am. Chem. Soc., 1998, 120, 342; (m) F. Villar, T. Kolly-Kovac, O. Equey and P. Renaud, Chem. Eur. J., 2003, 9, 1566; (n) T. M. Nguyen, R. J. Seifert, D. R. Mowrey and D. Lee, Org. Lett., 2002, 4, 3959; (o) T. Ishikawa, K. Shimizu, H. Ishii, S. Ikeda and S. Saito, J. Org. Chem., 2001, 66, 3834; (p) K. Ohmori, Y. Hachisu, T. Suzuki and K. Suzuki, Tetrahedron Lett., 2002, 43, 1031; (q) Y.-i. Fukuda, H. Sasaki, M. Shindo and K. Shishido, Tetrahedron Lett., 2002, 43, 2047; (r) P. A. Evans, J. Cui and G. P. Buffone, Angew. Chem., Int. Ed., 2003, 42, 1734.
8. Representative examples involving diastereotopic alkene and alkyne groups: (a) S. F. Martin, S. K. Davidsen and T. A. Puckette, J. Org. Chem., 1987, 52, 1962; (b) S. F. Martin and C. L. Campbell, J. Org. Chem., 1988, 53, 3184; (c) P. Wipf and Y. Kim, Tetrahedron Lett., 1992, 33, 5477; (d) P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848; (e) D. Bland, D. J. Hart and S. Lacoutiere, Tetrahedron, 1997, 53, 8871; (f) D. Bland, G. Chambournier, V. Dragan and D. J. Hart, Tetrahedron, 1999, 55, 8953; (g) H. Fujioka, S. Kitagaki, N. Ohno, H. Kitagawa, Y. Kita and K. Matsumoto, Tetrahedron: Asymmetry, 1994, 5, 333; (h) M. C. Carreño, M. P. González, M. Ribagorda and K. N. Houk, J. Org. Chem., 1998, 63, 3687; (i) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; (J) M. Suginome, Y. Yamamoto, K. Fujii and Y. Ito, J. Am. Chem. Soc., 1995, 117, 9608; (k) D. P. Curran, S. J. Geib and C.-H. Lin, Tetrahedron: Asymmetry, 1994, 5, 199; (l) D. P. Curran, C.-H. Lin, N. DeMello and J. Junggebauer, J. Am. Chem. Soc., 1998, 120, 342; (m) F. Villar, T. Kolly-Kovac, O. Equey and P. Renaud, Chem. Eur. J., 2003, 9, 1566; (n) T. M. Nguyen, R. J. Seifert, D. R. Mowrey and D. Lee, Org. Lett., 2002, 4, 3959; (o) T. Ishikawa, K. Shimizu, H. Ishii, S. Ikeda and S. Saito, J. Org. Chem., 2001, 66, 3834; (p) K. Ohmori, Y. Hachisu, T. Suzuki and K. Suzuki, Tetrahedron Lett., 2002, 43, 1031; (q) Y.-i. Fukuda, H. Sasaki, M. Shindo and K. Shishido, Tetrahedron Lett., 2002, 43, 2047; (r) P. A. Evans, J. Cui and G. P. Buffone, Angew. Chem., Int. Ed., 2003, 42, 1734.
9. Representative examples involving diastereotopic alkene and alkyne groups: (a) S. F. Martin, S. K. Davidsen and T. A. Puckette, J. Org. Chem., 1987, 52, 1962; (b) S. F. Martin and C. L. Campbell, J. Org. Chem., 1988, 53, 3184; (c) P. Wipf and Y. Kim, Tetrahedron Lett., 1992, 33, 5477; (d) P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848; (e) D. Bland, D. J. Hart and S. Lacoutiere, Tetrahedron, 1997, 53, 8871; (f) D. Bland, G. Chambournier, V. Dragan and D. J. Hart, Tetrahedron, 1999, 55, 8953; (g) H. Fujioka, S. Kitagaki, N. Ohno, H. Kitagawa, Y. Kita and K. Matsumoto, Tetrahedron: Asymmetry, 1994, 5, 333; (h) M. C. Carreño, M. P. González, M. Ribagorda and K. N. Houk, J. Org. Chem., 1998, 63, 3687; (i) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; (J) M. Suginome, Y. Yamamoto, K. Fujii and Y. Ito, J. Am. Chem. Soc., 1995, 117, 9608; (k) D. P. Curran, S. J. Geib and C.-H. Lin, Tetrahedron: Asymmetry, 1994, 5, 199; (l) D. P. Curran, C.-H. Lin, N. DeMello and J. Junggebauer, J. Am. Chem. Soc., 1998, 120, 342; (m) F. Villar, T. Kolly-Kovac, O. Equey and P. Renaud, Chem. Eur. J., 2003, 9, 1566; (n) T. M. Nguyen, R. J. Seifert, D. R. Mowrey and D. Lee, Org. Lett., 2002, 4, 3959; (o) T. Ishikawa, K. Shimizu, H. Ishii, S. Ikeda and S. Saito, J. Org. Chem., 2001, 66, 3834; (p) K. Ohmori, Y. Hachisu, T. Suzuki and K. Suzuki, Tetrahedron Lett., 2002, 43, 1031; (q) Y.-i. Fukuda, H. Sasaki, M. Shindo and K. Shishido, Tetrahedron Lett., 2002, 43, 2047; (r) P. A. Evans, J. Cui and G. P. Buffone, Angew. Chem., Int. Ed., 2003, 42, 1734.
10. Representative examples involving diastereotopic alkene and alkyne groups: (a) S. F. Martin, S. K. Davidsen and T. A. Puckette, J. Org. Chem., 1987, 52, 1962; (b) S. F. Martin and C. L. Campbell, J. Org. Chem., 1988, 53, 3184; (c) P. Wipf and Y. Kim, Tetrahedron Lett., 1992, 33, 5477; (d) P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848; (e) D. Bland, D. J. Hart and S. Lacoutiere, Tetrahedron, 1997, 53, 8871; (f) D. Bland, G. Chambournier, V. Dragan and D. J. Hart, Tetrahedron, 1999, 55, 8953; (g) H. Fujioka, S. Kitagaki, N. Ohno, H. Kitagawa, Y. Kita and K. Matsumoto, Tetrahedron: Asymmetry, 1994, 5, 333; (h) M. C. Carreño, M. P. González, M. Ribagorda and K. N. Houk, J. Org. Chem., 1998, 63, 3687; (i) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; (J) M. Suginome, Y. Yamamoto, K. Fujii and Y. Ito, J. Am. Chem. Soc., 1995, 117, 9608; (k) D. P. Curran, S. J. Geib and C.-H. Lin, Tetrahedron: Asymmetry, 1994, 5, 199; (l) D. P. Curran, C.-H. Lin, N. DeMello and J. Junggebauer, J. Am. Chem. Soc., 1998, 120, 342; (m) F. Villar, T. Kolly-Kovac, O. Equey and P. Renaud, Chem. Eur. J., 2003, 9, 1566; (n) T. M. Nguyen, R. J. Seifert, D. R. Mowrey and D. Lee, Org. Lett., 2002, 4, 3959; (o) T. Ishikawa, K. Shimizu, H. Ishii, S. Ikeda and S. Saito, J. Org. Chem., 2001, 66, 3834; (p) K. Ohmori, Y. Hachisu, T. Suzuki and K. Suzuki, Tetrahedron Lett., 2002, 43, 1031; (q) Y.-i. Fukuda, H. Sasaki, M. Shindo and K. Shishido, Tetrahedron Lett., 2002, 43, 2047; (r) P. A. Evans, J. Cui and G. P. Buffone, Angew. Chem., Int. Ed., 2003, 42, 1734.
11. Representative examples involving diastereotopic alkene and alkyne groups: (a) S. F. Martin, S. K. Davidsen and T. A. Puckette, J. Org. Chem., 1987, 52, 1962; (b) S. F. Martin and C. L. Campbell, J. Org. Chem., 1988, 53, 3184; (c) P. Wipf and Y. Kim, Tetrahedron Lett., 1992, 33, 5477; (d) P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848; (e) D. Bland, D. J. Hart and S. Lacoutiere, Tetrahedron, 1997, 53, 8871; (f) D. Bland, G. Chambournier, V. Dragan and D. J. Hart, Tetrahedron, 1999, 55, 8953; (g) H. Fujioka, S. Kitagaki, N. Ohno, H. Kitagawa, Y. Kita and K. Matsumoto, Tetrahedron: Asymmetry, 1994, 5, 333; (h) M. C. Carreño, M. P. González, M. Ribagorda and K. N. Houk, J. Org. Chem., 1998, 63, 3687; (i) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; (J) M. Suginome, Y. Yamamoto, K. Fujii and Y. Ito, J. Am. Chem. Soc., 1995, 117, 9608; (k) D. P. Curran, S. J. Geib and C.-H. Lin, Tetrahedron: Asymmetry, 1994, 5, 199; (l) D. P. Curran, C.-H. Lin, N. DeMello and J. Junggebauer, J. Am. Chem. Soc., 1998, 120, 342; (m) F. Villar, T. Kolly-Kovac, O. Equey and P. Renaud, Chem. Eur. J., 2003, 9, 1566; (n) T. M. Nguyen, R. J. Seifert, D. R. Mowrey and D. Lee, Org. Lett., 2002, 4, 3959; (o) T. Ishikawa, K. Shimizu, H. Ishii, S. Ikeda and S. Saito, J. Org. Chem., 2001, 66, 3834; (p) K. Ohmori, Y. Hachisu, T. Suzuki and K. Suzuki, Tetrahedron Lett., 2002, 43, 1031; (q) Y.-i. Fukuda, H. Sasaki, M. Shindo and K. Shishido, Tetrahedron Lett., 2002, 43, 2047; (r) P. A. Evans, J. Cui and G. P. Buffone, Angew. Chem., Int. Ed., 2003, 42, 1734.
12. Representative examples involving diastereotopic alkene and alkyne groups: (a) S. F. Martin, S. K. Davidsen and T. A. Puckette, J. Org. Chem., 1987, 52, 1962; (b) S. F. Martin and C. L. Campbell, J. Org. Chem., 1988, 53, 3184; (c) P. Wipf and Y. Kim, Tetrahedron Lett., 1992, 33, 5477; (d) P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848; (e) D. Bland, D. J. Hart and S. Lacoutiere, Tetrahedron, 1997, 53, 8871; (f) D. Bland, G. Chambournier, V. Dragan and D. J. Hart, Tetrahedron, 1999, 55, 8953; (g) H. Fujioka, S. Kitagaki, N. Ohno, H. Kitagawa, Y. Kita and K. Matsumoto, Tetrahedron: Asymmetry, 1994, 5, 333; (h) M. C. Carreño, M. P. González, M. Ribagorda and K. N. Houk, J. Org. Chem., 1998, 63, 3687; (i) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; (J) M. Suginome, Y. Yamamoto, K. Fujii and Y. Ito, J. Am. Chem. Soc., 1995, 117, 9608; (k) D. P. Curran, S. J. Geib and C.-H. Lin, Tetrahedron: Asymmetry, 1994, 5, 199; (l) D. P. Curran, C.-H. Lin, N. DeMello and J. Junggebauer, J. Am. Chem. Soc., 1998, 120, 342; (m) F. Villar, T. Kolly-Kovac, O. Equey and P. Renaud, Chem. Eur. J., 2003, 9, 1566; (n) T. M. Nguyen, R. J. Seifert, D. R. Mowrey and D. Lee, Org. Lett., 2002, 4, 3959; (o) T. Ishikawa, K. Shimizu, H. Ishii, S. Ikeda and S. Saito, J. Org. Chem., 2001, 66, 3834; (p) K. Ohmori, Y. Hachisu, T. Suzuki and K. Suzuki, Tetrahedron Lett., 2002, 43, 1031; (q) Y.-i. Fukuda, H. Sasaki, M. Shindo and K. Shishido, Tetrahedron Lett., 2002, 43, 2047; (r) P. A. Evans, J. Cui and G. P. Buffone, Angew. Chem., Int. Ed., 2003, 42, 1734.
13. Representative examples involving diastereotopic alkene and alkyne groups: (a) S. F. Martin, S. K. Davidsen and T. A. Puckette, J. Org. Chem., 1987, 52, 1962; (b) S. F. Martin and C. L. Campbell, J. Org. Chem., 1988, 53, 3184; (c) P. Wipf and Y. Kim, Tetrahedron Lett., 1992, 33, 5477; (d) P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848; (e) D. Bland, D. J. Hart and S. Lacoutiere, Tetrahedron, 1997, 53, 8871; (f) D. Bland, G. Chambournier, V. Dragan and D. J. Hart, Tetrahedron, 1999, 55, 8953; (g) H. Fujioka, S. Kitagaki, N. Ohno, H. Kitagawa, Y. Kita and K. Matsumoto, Tetrahedron: Asymmetry, 1994, 5, 333; (h) M. C. Carreño, M. P. González, M. Ribagorda and K. N. Houk, J. Org. Chem., 1998, 63, 3687; (i) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; (J) M. Suginome, Y. Yamamoto, K. Fujii and Y. Ito, J. Am. Chem. Soc., 1995, 117, 9608; (k) D. P. Curran, S. J. Geib and C.-H. Lin, Tetrahedron: Asymmetry, 1994, 5, 199; (l) D. P. Curran, C.-H. Lin, N. DeMello and J. Junggebauer, J. Am. Chem. Soc., 1998, 120, 342; (m) F. Villar, T. Kolly-Kovac, O. Equey and P. Renaud, Chem. Eur. J., 2003, 9, 1566; (n) T. M. Nguyen, R. J. Seifert, D. R. Mowrey and D. Lee, Org. Lett., 2002, 4, 3959; (o) T. Ishikawa, K. Shimizu, H. Ishii, S. Ikeda and S. Saito, J. Org. Chem., 2001, 66, 3834; (p) K. Ohmori, Y. Hachisu, T. Suzuki and K. Suzuki, Tetrahedron Lett., 2002, 43, 1031; (q) Y.-i. Fukuda, H. Sasaki, M. Shindo and K. Shishido, Tetrahedron Lett., 2002, 43, 2047; (r) P. A. Evans, J. Cui and G. P. Buffone, Angew. Chem., Int. Ed., 2003, 42, 1734.
14. Representative examples involving diastereotopic alkene and alkyne groups: (a) S. F. Martin, S. K. Davidsen and T. A. Puckette, J. Org. Chem., 1987, 52, 1962; (b) S. F. Martin and C. L. Campbell, J. Org. Chem., 1988, 53, 3184; (c) P. Wipf and Y. Kim, Tetrahedron Lett., 1992, 33, 5477; (d) P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848; (e) D. Bland, D. J. Hart and S. Lacoutiere, Tetrahedron, 1997, 53, 8871; (f) D. Bland, G. Chambournier, V. Dragan and D. J. Hart, Tetrahedron, 1999, 55, 8953; (g) H. Fujioka, S. Kitagaki, N. Ohno, H. Kitagawa, Y. Kita and K. Matsumoto, Tetrahedron: Asymmetry, 1994, 5, 333; (h) M. C. Carreño, M. P. González, M. Ribagorda and K. N. Houk, J. Org. Chem., 1998, 63, 3687; (i) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; (J) M. Suginome, Y. Yamamoto, K. Fujii and Y. Ito, J. Am. Chem. Soc., 1995, 117, 9608; (k) D. P. Curran, S. J. Geib and C.-H. Lin, Tetrahedron: Asymmetry, 1994, 5, 199; (l) D. P. Curran, C.-H. Lin, N. DeMello and J. Junggebauer, J. Am. Chem. Soc., 1998, 120, 342; (m) F. Villar, T. Kolly-Kovac, O. Equey and P. Renaud, Chem. Eur. J., 2003, 9, 1566; (n) T. M. Nguyen, R. J. Seifert, D. R. Mowrey and D. Lee, Org. Lett., 2002, 4, 3959; (o) T. Ishikawa, K. Shimizu, H. Ishii, S. Ikeda and S. Saito, J. Org. Chem., 2001, 66, 3834; (p) K. Ohmori, Y. Hachisu, T. Suzuki and K. Suzuki, Tetrahedron Lett., 2002, 43, 1031; (q) Y.-i. Fukuda, H. Sasaki, M. Shindo and K. Shishido, Tetrahedron Lett., 2002, 43, 2047; (r) P. A. Evans, J. Cui and G. P. Buffone, Angew. Chem., Int. Ed., 2003, 42, 1734.
15. Representative examples involving diastereotopic alkene and alkyne groups: (a) S. F. Martin, S. K. Davidsen and T. A. Puckette, J. Org. Chem., 1987, 52, 1962; (b) S. F. Martin and C. L. Campbell, J. Org. Chem., 1988, 53, 3184; (c) P. Wipf and Y. Kim, Tetrahedron Lett., 1992, 33, 5477; (d) P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848; (e) D. Bland, D. J. Hart and S. Lacoutiere, Tetrahedron, 1997, 53, 8871; (f) D. Bland, G. Chambournier, V. Dragan and D. J. Hart, Tetrahedron, 1999, 55, 8953; (g) H. Fujioka, S. Kitagaki, N. Ohno, H. Kitagawa, Y. Kita and K. Matsumoto, Tetrahedron: Asymmetry, 1994, 5, 333; (h) M. C. Carreño, M. P. González, M. Ribagorda and K. N. Houk, J. Org. Chem., 1998, 63, 3687; (i) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; (J) M. Suginome, Y. Yamamoto, K. Fujii and Y. Ito, J. Am. Chem. Soc., 1995, 117, 9608; (k) D. P. Curran, S. J. Geib and C.-H. Lin, Tetrahedron: Asymmetry, 1994, 5, 199; (l) D. P. Curran, C.-H. Lin, N. DeMello and J. Junggebauer, J. Am. Chem. Soc., 1998, 120, 342; (m) F. Villar, T. Kolly-Kovac, O. Equey and P. Renaud, Chem. Eur. J., 2003, 9, 1566; (n) T. M. Nguyen, R. J. Seifert, D. R. Mowrey and D. Lee, Org. Lett., 2002, 4, 3959; (o) T. Ishikawa, K. Shimizu, H. Ishii, S. Ikeda and S. Saito, J. Org. Chem., 2001, 66, 3834; (p) K. Ohmori, Y. Hachisu, T. Suzuki and K. Suzuki, Tetrahedron Lett., 2002, 43, 1031; (q) Y.-i. Fukuda, H. Sasaki, M. Shindo and K. Shishido, Tetrahedron Lett., 2002, 43, 2047; (r) P. A. Evans, J. Cui and G. P. Buffone, Angew. Chem., Int. Ed., 2003, 42, 1734.
16. Representative examples involving diastereotopic alkene and alkyne groups: (a) S. F. Martin, S. K. Davidsen and T. A. Puckette, J. Org. Chem., 1987, 52, 1962; (b) S. F. Martin and C. L. Campbell, J. Org. Chem., 1988, 53, 3184; (c) P. Wipf and Y. Kim, Tetrahedron Lett., 1992, 33, 5477; (d) P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848; (e) D. Bland, D. J. Hart and S. Lacoutiere, Tetrahedron, 1997, 53, 8871; (f) D. Bland, G. Chambournier, V. Dragan and D. J. Hart, Tetrahedron, 1999, 55, 8953; (g) H. Fujioka, S. Kitagaki, N. Ohno, H. Kitagawa, Y. Kita and K. Matsumoto, Tetrahedron: Asymmetry, 1994, 5, 333; (h) M. C. Carreño, M. P. González, M. Ribagorda and K. N. Houk, J. Org. Chem., 1998, 63, 3687; (i) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; (J) M. Suginome, Y. Yamamoto, K. Fujii and Y. Ito, J. Am. Chem. Soc., 1995, 117, 9608; (k) D. P. Curran, S. J. Geib and C.-H. Lin, Tetrahedron: Asymmetry, 1994, 5, 199; (l) D. P. Curran, C.-H. Lin, N. DeMello and J. Junggebauer, J. Am. Chem. Soc., 1998, 120, 342; (m) F. Villar, T. Kolly-Kovac, O. Equey and P. Renaud, Chem. Eur. J., 2003, 9, 1566; (n) T. M. Nguyen, R. J. Seifert, D. R. Mowrey and D. Lee, Org. Lett., 2002, 4, 3959; (o) T. Ishikawa, K. Shimizu, H. Ishii, S. Ikeda and S. Saito, J. Org. Chem., 2001, 66, 3834; (p) K. Ohmori, Y. Hachisu, T. Suzuki and K. Suzuki, Tetrahedron Lett., 2002, 43, 1031; (q) Y.-i. Fukuda, H. Sasaki, M. Shindo and K. Shishido, Tetrahedron Lett., 2002, 43, 2047; (r) P. A. Evans, J. Cui and G. P. Buffone, Angew. Chem., Int. Ed., 2003, 42, 1734.
17. Representative examples involving diastereotopic alkene and alkyne groups: (a) S. F. Martin, S. K. Davidsen and T. A. Puckette, J. Org. Chem., 1987, 52, 1962; (b) S. F. Martin and C. L. Campbell, J. Org. Chem., 1988, 53, 3184; (c) P. Wipf and Y. Kim, Tetrahedron Lett., 1992, 33, 5477; (d) P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848; (e) D. Bland, D. J. Hart and S. Lacoutiere, Tetrahedron, 1997, 53, 8871; (f) D. Bland, G. Chambournier, V. Dragan and D. J. Hart, Tetrahedron, 1999, 55, 8953; (g) H. Fujioka, S. Kitagaki, N. Ohno, H. Kitagawa, Y. Kita and K. Matsumoto, Tetrahedron: Asymmetry, 1994, 5, 333; (h) M. C. Carreño, M. P. González, M. Ribagorda and K. N. Houk, J. Org. Chem., 1998, 63, 3687; (i) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; (J) M. Suginome, Y. Yamamoto, K. Fujii and Y. Ito, J. Am. Chem. Soc., 1995, 117, 9608; (k) D. P. Curran, S. J. Geib and C.-H. Lin, Tetrahedron: Asymmetry, 1994, 5, 199; (l) D. P. Curran, C.-H. Lin, N. DeMello and J. Junggebauer, J. Am. Chem. Soc., 1998, 120, 342; (m) F. Villar, T. Kolly-Kovac, O. Equey and P. Renaud, Chem. Eur. J., 2003, 9, 1566; (n) T. M. Nguyen, R. J. Seifert, D. R. Mowrey and D. Lee, Org. Lett., 2002, 4, 3959; (o) T. Ishikawa, K. Shimizu, H. Ishii, S. Ikeda and S. Saito, J. Org. Chem., 2001, 66, 3834; (p) K. Ohmori, Y. Hachisu, T. Suzuki and K. Suzuki, Tetrahedron Lett., 2002, 43, 1031; (q) Y.-i. Fukuda, H. Sasaki, M. Shindo and K. Shishido, Tetrahedron Lett., 2002, 43, 2047; (r) P. A. Evans, J. Cui and G. P. Buffone, Angew. Chem., Int. Ed., 2003, 42, 1734.
18. Representative examples involving diastereotopic alkene and alkyne groups: (a) S. F. Martin, S. K. Davidsen and T. A. Puckette, J. Org. Chem., 1987, 52, 1962; (b) S. F. Martin and C. L. Campbell, J. Org. Chem., 1988, 53, 3184; (c) P. Wipf and Y. Kim, Tetrahedron Lett., 1992, 33, 5477; (d) P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848; (e) D. Bland, D. J. Hart and S. Lacoutiere, Tetrahedron, 1997, 53, 8871; (f) D. Bland, G. Chambournier, V. Dragan and D. J. Hart, Tetrahedron, 1999, 55, 8953; (g) H. Fujioka, S. Kitagaki, N. Ohno, H. Kitagawa, Y. Kita and K. Matsumoto, Tetrahedron: Asymmetry, 1994, 5, 333; (h) M. C. Carreño, M. P. González, M. Ribagorda and K. N. Houk, J. Org. Chem., 1998, 63, 3687; (i) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; (J) M. Suginome, Y. Yamamoto, K. Fujii and Y. Ito, J. Am. Chem. Soc., 1995, 117, 9608; (k) D. P. Curran, S. J. Geib and C.-H. Lin, Tetrahedron: Asymmetry, 1994, 5, 199; (l) D. P. Curran, C.-H. Lin, N. DeMello and J. Junggebauer, J. Am. Chem. Soc., 1998, 120, 342; (m) F. Villar, T. Kolly-Kovac, O. Equey and P. Renaud, Chem. Eur. J., 2003, 9, 1566; (n) T. M. Nguyen, R. J. Seifert, D. R. Mowrey and D. Lee, Org. Lett., 2002, 4, 3959; (o) T. Ishikawa, K. Shimizu, H. Ishii, S. Ikeda and S. Saito, J. Org. Chem., 2001, 66, 3834; (p) K. Ohmori, Y. Hachisu, T. Suzuki and K. Suzuki, Tetrahedron Lett., 2002, 43, 1031; (q) Y.-i. Fukuda, H. Sasaki, M. Shindo and K. Shishido, Tetrahedron Lett., 2002, 43, 2047; (r) P. A. Evans, J. Cui and G. P. Buffone, Angew. Chem., Int. Ed., 2003, 42, 1734.
19. Representative examples involving diastereotopic alkene and alkyne groups: (a) S. F. Martin, S. K. Davidsen and T. A. Puckette, J. Org. Chem., 1987, 52, 1962; (b) S. F. Martin and C. L. Campbell, J. Org. Chem., 1988, 53, 3184; (c) P. Wipf and Y. Kim, Tetrahedron Lett., 1992, 33, 5477; (d) P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848; (e) D. Bland, D. J. Hart and S. Lacoutiere, Tetrahedron, 1997, 53, 8871; (f) D. Bland, G. Chambournier, V. Dragan and D. J. Hart, Tetrahedron, 1999, 55, 8953; (g) H. Fujioka, S. Kitagaki, N. Ohno, H. Kitagawa, Y. Kita and K. Matsumoto, Tetrahedron: Asymmetry, 1994, 5, 333; (h) M. C. Carreño, M. P. González, M. Ribagorda and K. N. Houk, J. Org. Chem., 1998, 63, 3687; (i) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; (J) M. Suginome, Y. Yamamoto, K. Fujii and Y. Ito, J. Am. Chem. Soc., 1995, 117, 9608; (k) D. P. Curran, S. J. Geib and C.-H. Lin, Tetrahedron: Asymmetry, 1994, 5, 199; (l) D. P. Curran, C.-H. Lin, N. DeMello and J. Junggebauer, J. Am. Chem. Soc., 1998, 120, 342; (m) F. Villar, T. Kolly-Kovac, O. Equey and P. Renaud, Chem. Eur. J., 2003, 9, 1566; (n) T. M. Nguyen, R. J. Seifert, D. R. Mowrey and D. Lee, Org. Lett., 2002, 4, 3959; (o) T. Ishikawa, K. Shimizu, H. Ishii, S. Ikeda and S. Saito, J. Org. Chem., 2001, 66, 3834; (p) K. Ohmori, Y. Hachisu, T. Suzuki and K. Suzuki, Tetrahedron Lett., 2002, 43, 1031; (q) Y.-i. Fukuda, H. Sasaki, M. Shindo and K. Shishido, Tetrahedron Lett., 2002, 43, 2047; (r) P. A. Evans, J. Cui and G. P. Buffone, Angew. Chem., Int. Ed., 2003, 42, 1734.
20. Representative examples involving diastereotopic alkene and alkyne groups: (a) S. F. Martin, S. K. Davidsen and T. A. Puckette, J. Org. Chem., 1987, 52, 1962; (b) S. F. Martin and C. L. Campbell, J. Org. Chem., 1988, 53, 3184; (c) P. Wipf and Y. Kim, Tetrahedron Lett., 1992, 33, 5477; (d) P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848; (e) D. Bland, D. J. Hart and S. Lacoutiere, Tetrahedron, 1997, 53, 8871; (f) D. Bland, G. Chambournier, V. Dragan and D. J. Hart, Tetrahedron, 1999, 55, 8953; (g) H. Fujioka, S. Kitagaki, N. Ohno, H. Kitagawa, Y. Kita and K. Matsumoto, Tetrahedron: Asymmetry, 1994, 5, 333; (h) M. C. Carreño, M. P. González, M. Ribagorda and K. N. Houk, J. Org. Chem., 1998, 63, 3687; (i) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; (J) M. Suginome, Y. Yamamoto, K. Fujii and Y. Ito, J. Am. Chem. Soc., 1995, 117, 9608; (k) D. P. Curran, S. J. Geib and C.-H. Lin, Tetrahedron: Asymmetry, 1994, 5, 199; (l) D. P. Curran, C.-H. Lin, N. DeMello and J. Junggebauer, J. Am. Chem. Soc., 1998, 120, 342; (m) F. Villar, T. Kolly-Kovac, O. Equey and P. Renaud, Chem. Eur. J., 2003, 9, 1566; (n) T. M. Nguyen, R. J. Seifert, D. R. Mowrey and D. Lee, Org. Lett., 2002, 4, 3959; (o) T. Ishikawa, K. Shimizu, H. Ishii, S. Ikeda and S. Saito, J. Org. Chem., 2001, 66, 3834; (p) K. Ohmori, Y. Hachisu, T. Suzuki and K. Suzuki, Tetrahedron Lett., 2002, 43, 1031; (q) Y.-i. Fukuda, H. Sasaki, M. Shindo and K. Shishido, Tetrahedron Lett., 2002, 43, 2047; (r) P. A. Evans, J. Cui and G. P. Buffone, Angew. Chem., Int. Ed., 2003, 42, 1734.
21. Representative examples involving diastereotopic alkene and alkyne groups: (a) S. F. Martin, S. K. Davidsen and T. A. Puckette, J. Org. Chem., 1987, 52, 1962; (b) S. F. Martin and C. L. Campbell, J. Org. Chem., 1988, 53, 3184; (c) P. Wipf and Y. Kim, Tetrahedron Lett., 1992, 33, 5477; (d) P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848; (e) D. Bland, D. J. Hart and S. Lacoutiere, Tetrahedron, 1997, 53, 8871; (f) D. Bland, G. Chambournier, V. Dragan and D. J. Hart, Tetrahedron, 1999, 55, 8953; (g) H. Fujioka, S. Kitagaki, N. Ohno, H. Kitagawa, Y. Kita and K. Matsumoto, Tetrahedron: Asymmetry, 1994, 5, 333; (h) M. C. Carreño, M. P. González, M. Ribagorda and K. N. Houk, J. Org. Chem., 1998, 63, 3687; (i) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; (J) M. Suginome, Y. Yamamoto, K. Fujii and Y. Ito, J. Am. Chem. Soc., 1995, 117, 9608; (k) D. P. Curran, S. J. Geib and C.-H. Lin, Tetrahedron: Asymmetry, 1994, 5, 199; (l) D. P. Curran, C.-H. Lin, N. DeMello and J. Junggebauer, J. Am. Chem. Soc., 1998, 120, 342; (m) F. Villar, T. Kolly-Kovac, O. Equey and P. Renaud, Chem. Eur. J., 2003, 9, 1566; (n) T. M. Nguyen, R. J. Seifert, D. R. Mowrey and D. Lee, Org. Lett., 2002, 4, 3959; (o) T. Ishikawa, K. Shimizu, H. Ishii, S. Ikeda and S. Saito, J. Org. Chem., 2001, 66, 3834; (p) K. Ohmori, Y. Hachisu, T. Suzuki and K. Suzuki, Tetrahedron Lett., 2002, 43, 1031; (q) Y.-i. Fukuda, H. Sasaki, M. Shindo and K. Shishido, Tetrahedron Lett., 2002, 43, 2047; (r) P. A. Evans, J. Cui and G. P. Buffone, Angew. Chem., Int. Ed., 2003, 42, 1734.
22. Representative examples involving diastereotopic alkene and alkyne groups: (a) S. F. Martin, S. K. Davidsen and T. A. Puckette, J. Org. Chem., 1987, 52, 1962; (b) S. F. Martin and C. L. Campbell, J. Org. Chem., 1988, 53, 3184; (c) P. Wipf and Y. Kim, Tetrahedron Lett., 1992, 33, 5477; (d) P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848; (e) D. Bland, D. J. Hart and S. Lacoutiere, Tetrahedron, 1997, 53, 8871; (f) D. Bland, G. Chambournier, V. Dragan and D. J. Hart, Tetrahedron, 1999, 55, 8953; (g) H. Fujioka, S. Kitagaki, N. Ohno, H. Kitagawa, Y. Kita and K. Matsumoto, Tetrahedron: Asymmetry, 1994, 5, 333; (h) M. C. Carreño, M. P. González, M. Ribagorda and K. N. Houk, J. Org. Chem., 1998, 63, 3687; (i) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; (J) M. Suginome, Y. Yamamoto, K. Fujii and Y. Ito, J. Am. Chem. Soc., 1995, 117, 9608; (k) D. P. Curran, S. J. Geib and C.-H. Lin, Tetrahedron: Asymmetry, 1994, 5, 199; (l) D. P. Curran, C.-H. Lin, N. DeMello and J. Junggebauer, J. Am. Chem. Soc., 1998, 120, 342; (m) F. Villar, T. Kolly-Kovac, O. Equey and P. Renaud, Chem. Eur. J., 2003, 9, 1566; (n) T. M. Nguyen, R. J. Seifert, D. R. Mowrey and D. Lee, Org. Lett., 2002, 4, 3959; (o) T. Ishikawa, K. Shimizu, H. Ishii, S. Ikeda and S. Saito, J. Org. Chem., 2001, 66, 3834; (p) K. Ohmori, Y. Hachisu, T. Suzuki and K. Suzuki, Tetrahedron Lett., 2002, 43, 1031; (q) Y.-i. Fukuda, H. Sasaki, M. Shindo and K. Shishido, Tetrahedron Lett., 2002, 43, 2047; (r) P. A. Evans, J. Cui and G. P. Buffone, Angew. Chem., Int. Ed., 2003, 42, 1734.
23. J. W. Cubbage, Y. Guo, R. D. McCulla and W. S. Jenks, J. Org. Chem., 2001, 66, 8722 and references therein.
24. S. Braverman, in The Chemistry of Sulfenic Acids and their Derivatives, ed. S. Patai, Wiley, New York, 1990, p. 311.
25. (a) D. N. Jones, D. R. Hill, D. A. Lewton and C. Sheppard, J. Chem. Soc., Perkin Trans. 1, 1977, 1574;
26. (b) D. N. Jones, in Perspectives in the Organic Chemistry of Sulfur, ed. B. Zwanenburg and A. J. H. Klunder, Elsevier, New York, 1987, p. 189.
27. For a review on synthetic strategies towards the total synthesis of breynolide see: A. B. Smith and J. R. Empfield, Chem. Pharm. Bull., 1999, 47, 1671.
28. For other examples where the sterochemical control element is designed also to ultimately reside in the target compound see refs 3a,d,e,f,j.
29. A. G. Schultz and L. O. Lockwood, J. Org. Chem., 2000, 65, 6354.
30. Reviews on the preparation and application of β-ketosulfoxides: (a) M. Carmen Carreño, Chem. Rev., 1995, 95, 1717; (b) G. Solladié and M. Carmen Carreño, in Organosulfur Chemistry, Synthetic Aspects, ed. P. Page, Academic Press, New York, 1995, p. 1.
31. Reviews on the preparation and application of β-ketosulfoxides: (a) M. Carmen Carreño, Chem. Rev., 1995, 95, 1717; (b) G. Solladié and M. Carmen Carreño, in Organosulfur Chemistry, Synthetic Aspects, ed. P. Page, Academic Press, New York, 1995, p. 1.
32. All chiral compounds used in this study are racemic.
33. (a) I. Fernandez, J. M. Llera, F. Zorrilla and F. Alcudia, Tetrahearon, 1989, 45, 2703;
34. (b) F. Alcudia, I. Fernandez, J. M. Llera and F. Zorrilla, An. Quim., 1988, 84, 333.
35. Yields for the preparation of 11b-g have not been optimised.
36. 3, Ac, Bz, Ts, TMS, t-Bu], which show little variation with the nature of X: E. L. Eliel, S. H. Wilen and L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994, p. 695.
37. For an example of lowering the temperature of sulfoxide elimination through structural variation see: H. Adams, J. C. Anderson, R. Bell, D. N. Jones, M. R. Peel and N. C. O. Tomkinson, J. Chem. Soc., Perkin. Trans. 1, 1998, 3967.