The diastereoselective synthesis of quaternary substituted thioindolines from sulfur ylide intermediates

Journal of Organic Chemistry

Volumn 70, Issue 2, 2005, Pages 746-748

  Nyong, Abijah M ^a   Rainier, Jon D ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; RHODIUM; SUBSTITUTION REACTIONS;

DIASTEREOSELECTIVE SYNTHESIS; QUATERNARY SUBSTITUTION; VINYL DIAZOACETATES;

AROMATIC COMPOUNDS;

ACETIC ACID DERIVATIVE; INDOLE DERIVATIVE; RHODIUM COMPLEX; SULFUR DERIVATIVE;

ARTICLE; CLAISEN REARRANGEMENT; PROTEIN QUATERNARY STRUCTURE; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

AZA COMPOUNDS; CATALYSIS; INDOLES; MOLECULAR STRUCTURE; RHODIUM; STEREOISOMERISM; SULFUR COMPOUNDS; VINYL COMPOUNDS;

EID: 12344252561     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0482413     Document Type: Article

References (31)

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4. For a recent review covering approaches to the synthesis of indoles and indole alkaloids see: Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045.
5. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143, (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175, (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Feduoloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657. (j) Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666. (k) Onishi, T.; Sebahar, P. R.; Williams, R. M. Org. Lett. 2003, 5, 3135.
6. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143, (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175, (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Feduoloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657. (j) Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666. (k) Onishi, T.; Sebahar, P. R.; Williams, R. M. Org. Lett. 2003, 5, 3135.
7. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143, (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175, (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Feduoloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657. (j) Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666. (k) Onishi, T.; Sebahar, P. R.; Williams, R. M. Org. Lett. 2003, 5, 3135.
8. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143, (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175, (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Feduoloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657. (j) Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666. (k) Onishi, T.; Sebahar, P. R.; Williams, R. M. Org. Lett. 2003, 5, 3135.
9. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143, (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175, (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Feduoloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657. (j) Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666. (k) Onishi, T.; Sebahar, P. R.; Williams, R. M. Org. Lett. 2003, 5, 3135.
10. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143, (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175, (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Feduoloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657. (j) Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666. (k) Onishi, T.; Sebahar, P. R.; Williams, R. M. Org. Lett. 2003, 5, 3135.
11. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143, (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175, (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Feduoloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657. (j) Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666. (k) Onishi, T.; Sebahar, P. R.; Williams, R. M. Org. Lett. 2003, 5, 3135.
12. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143, (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175, (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Feduoloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657. (j) Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666. (k) Onishi, T.; Sebahar, P. R.; Williams, R. M. Org. Lett. 2003, 5, 3135.
13. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143, (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175, (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Feduoloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657. (j) Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666. (k) Onishi, T.; Sebahar, P. R.; Williams, R. M. Org. Lett. 2003, 5, 3135.
14. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143, (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175, (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Feduoloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657. (j) Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666. (k) Onishi, T.; Sebahar, P. R.; Williams, R. M. Org. Lett. 2003, 5, 3135.
15. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143, (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175, (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Feduoloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657. (j) Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666. (k) Onishi, T.; Sebahar, P. R.; Williams, R. M. Org. Lett. 2003, 5, 3135.
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19. We are aware of three other examples of ylide initiated [3,3]-sigmatropic rearrangements. See: (a) Nakano, H.; Ibata, T. Bull. Chem. Soc. Jpn. 1995, 68, 1393. (b) Wood, J. L.; Moniz, G. A.; Pflum, D. A.; Stoltz, B. M.; Holubec, A. A.; Dietrich, H.-J. J. Am. Chem. Soc. 1999, 121, 1748. (c) Wood, J. L.; Moniz, G. A. Org. Lett. 1999, 1, 371. (d) May, J. A.; Stoltz, B. M. J. Am. Chem. Soc. 2002, 124, 12426. (6) For relevant reviews covering ylide-initiated cascades see: (a) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (b) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911. (c) Hodgson, D. M.; Pierard, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50.
20. We are aware of three other examples of ylide initiated [3,3]-sigmatropic rearrangements. See: (a) Nakano, H.; Ibata, T. Bull. Chem. Soc. Jpn. 1995, 68, 1393. (b) Wood, J. L.; Moniz, G. A.; Pflum, D. A.; Stoltz, B. M.; Holubec, A. A.; Dietrich, H.-J. J. Am. Chem. Soc. 1999, 121, 1748. (c) Wood, J. L.; Moniz, G. A. Org. Lett. 1999, 1, 371. (d) May, J. A.; Stoltz, B. M. J. Am. Chem. Soc. 2002, 124, 12426. (6) For relevant reviews covering ylide-initiated cascades see: (a) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (b) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911. (c) Hodgson, D. M.; Pierard, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50.
21. We are aware of three other examples of ylide initiated [3,3]-sigmatropic rearrangements. See: (a) Nakano, H.; Ibata, T. Bull. Chem. Soc. Jpn. 1995, 68, 1393. (b) Wood, J. L.; Moniz, G. A.; Pflum, D. A.; Stoltz, B. M.; Holubec, A. A.; Dietrich, H.-J. J. Am. Chem. Soc. 1999, 121, 1748. (c) Wood, J. L.; Moniz, G. A. Org. Lett. 1999, 1, 371. (d) May, J. A.; Stoltz, B. M. J. Am. Chem. Soc. 2002, 124, 12426. (6) For relevant reviews covering ylide-initiated cascades see: (a) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (b) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911. (c) Hodgson, D. M.; Pierard, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50.
22. For relevant reviews covering ylide-initiated cascades see: (a) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
23. For relevant reviews covering ylide-initiated cascades see: (a) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (b) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911. (c) Hodgson, D. M.; Pierard, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50.
24. For relevant reviews covering ylide-initiated cascades see: (a) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (b) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911. (c) Hodgson, D. M.; Pierard, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50.
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30. The lower levels of diastereoselectivity observed with 12 may be due to a competitive direct C(3) alkylation of the unsubstituted vinyl carbenoid.
31. It is also possible that the lower levels of selectivity with 12 may be due to the formation of a configurationally unstable ylide. We thank a reviewer for this suggestion.