Asymmetric halo aldol reaction (AHA)

Organic Letters

Volumn 5, Issue 3, 2003, Pages 329-331

  Li, Guigen ^a   Xu, Xin ^a   Chen, Dianjun ^a   Timmons, Cody ^a   Carducci, Michael D ^a,b   Headley, Allan D ^a  

^a TEXAS TECH UNIVERSITY   (United States)

^b University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLIDINONE DERIVATIVE; FUSED HETEROCYCLIC RINGS;

ALDOL REACTION; ARTICLE; CHEMICAL BOND; CHIRALITY; DIASTEREOISOMER; STEREOCHEMISTRY; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY;

HETEROCYCLIC COMPOUNDS, 2-RING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXAZOLIDINONES;

EID: 0037504256     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027344+     Document Type: Article

References (35)

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12. Asymmetric catalytic reductive aldol reaction: Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528. Zhao, C.-X.; Bass, J.; Morken, J. P. Org. Lett. 2001, 3, 2839.
13. Three-component halo aldol reaction: (a) Wei, H.-X.; Caputo, T. D.; Purkiss, D. W.; Li, G. Tetrahedron 2000, 56, 2397. (b) Kataoka, T.; Kinoshita, H.; Kinoshita, S.; Iwamura, T.; Watanabe, S. Angew. Chem., Int. Ed. 2000, 39, 2358. (c) Wei, H.-X.; Gao, J.; Li, G. Tetrahedron Lett. 2001, 9119.
14. Three-component halo aldol reaction: (a) Wei, H.-X.; Caputo, T. D.; Purkiss, D. W.; Li, G. Tetrahedron 2000, 56, 2397. (b) Kataoka, T.; Kinoshita, H.; Kinoshita, S.; Iwamura, T.; Watanabe, S. Angew. Chem., Int. Ed. 2000, 39, 2358. (c) Wei, H.-X.; Gao, J.; Li, G. Tetrahedron Lett. 2001, 9119.
15. Three-component halo aldol reaction: (a) Wei, H.-X.; Caputo, T. D.; Purkiss, D. W.; Li, G. Tetrahedron 2000, 56, 2397. (b) Kataoka, T.; Kinoshita, H.; Kinoshita, S.; Iwamura, T.; Watanabe, S. Angew. Chem., Int. Ed. 2000, 39, 2358. (c) Wei, H.-X.; Gao, J.; Li, G. Tetrahedron Lett. 2001, 9119.
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18. (c) Han, Z.; Uehira, S.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 7854.
19. (d) Shi, M.; Jiang, J.-K.; Feng, Y.-S. Org. Lett. 2000, 2, 2397.
20. For reviews regarding the MBH reaction see: (a) Ciganek, E. Org. React. 1997, 51, 201. (b) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001. For a review regarding the synthesis of β-branched MBH adducts, see: (c) Li, G.; Hook, J.; Wei, H.-X. In Recent Research Developments in Organic & Bioorganic Chemistry; Transworld Research Network: 2001; Vol. 4, p 49.
21. For reviews regarding the MBH reaction see: (a) Ciganek, E. Org. React. 1997, 51, 201. (b) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001. For a review regarding the synthesis of β-branched MBH adducts, see: (c) Li, G.; Hook, J.; Wei, H.-X. In Recent Research Developments in Organic & Bioorganic Chemistry; Transworld Research Network: 2001; Vol. 4, p 49.
22. For reviews regarding the MBH reaction see: (a) Ciganek, E. Org. React. 1997, 51, 201. (b) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001. For a review regarding the synthesis of β-branched MBH adducts, see: (c) Li, G.; Hook, J.; Wei, H.-X. In Recent Research Developments in Organic & Bioorganic Chemistry; Transworld Research Network: 2001; Vol. 4, p 49.
23. For the MBH reaction without the direct use of any Lewis bases see: (a) ref 6a. (b) Li, G.; Gao, J.; Wei, H.-X.; Enright, M. Org. Lett. 2000, 2, 617. (c) Basavaiah, D.; Screenivasulu, B.; Rao, J. S. Tetrahedron Lett. 2001, 42, 1147. (d) Pei, W.; Wei, H.-X.; Li, G. J. Chem. Soc., Chem. Commun. 2002, 17, 1856. (e) Pei, W.; Wei, H.-X.; Li, G. J. Chem. Soc., Chem. Commun. 2002, 2412. For the MBH reaction using the combinations of Lewis acids and Lewis bases, see: (f) Uehira, S.; Han, Z.; Shinokubo, H.; Oshima, K. Org. Lett. 1999, 1, 1383. (g) Yagi, K.; Turitani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2002, 4, 3111. (h) Shi, M.; Jiang, J. K.; Cui, S. C.; Feng, Y. S. J. Chem. Soc., Perkin Trans. 1 2001, 390.
24. For the MBH reaction without the direct use of any Lewis bases see: (a) ref 6a. (b) Li, G.; Gao, J.; Wei, H.-X.; Enright, M. Org. Lett. 2000, 2, 617. (c) Basavaiah, D.; Screenivasulu, B.; Rao, J. S. Tetrahedron Lett. 2001, 42, 1147. (d) Pei, W.; Wei, H.-X.; Li, G. J. Chem. Soc., Chem. Commun. 2002, 17, 1856. (e) Pei, W.; Wei, H.-X.; Li, G. J. Chem. Soc., Chem. Commun. 2002, 2412. For the MBH reaction using the combinations of Lewis acids and Lewis bases, see: (f) Uehira, S.; Han, Z.; Shinokubo, H.; Oshima, K. Org. Lett. 1999, 1, 1383. (g) Yagi, K.; Turitani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2002, 4, 3111. (h) Shi, M.; Jiang, J. K.; Cui, S. C.; Feng, Y. S. J. Chem. Soc., Perkin Trans. 1 2001, 390.
25. For the MBH reaction without the direct use of any Lewis bases see: (a) ref 6a. (b) Li, G.; Gao, J.; Wei, H.-X.; Enright, M. Org. Lett. 2000, 2, 617. (c) Basavaiah, D.; Screenivasulu, B.; Rao, J. S. Tetrahedron Lett. 2001, 42, 1147. (d) Pei, W.; Wei, H.-X.; Li, G. J. Chem. Soc., Chem. Commun. 2002, 17, 1856. (e) Pei, W.; Wei, H.-X.; Li, G. J. Chem. Soc., Chem. Commun. 2002, 2412. For the MBH reaction using the combinations of Lewis acids and Lewis bases, see: (f) Uehira, S.; Han, Z.; Shinokubo, H.; Oshima, K. Org. Lett. 1999, 1, 1383. (g) Yagi, K.; Turitani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2002, 4, 3111. (h) Shi, M.; Jiang, J. K.; Cui, S. C.; Feng, Y. S. J. Chem. Soc., Perkin Trans. 1 2001, 390.
26. For the MBH reaction without the direct use of any Lewis bases see: (a) ref 6a. (b) Li, G.; Gao, J.; Wei, H.-X.; Enright, M. Org. Lett. 2000, 2, 617. (c) Basavaiah, D.; Screenivasulu, B.; Rao, J. S. Tetrahedron Lett. 2001, 42, 1147. (d) Pei, W.; Wei, H.-X.; Li, G. J. Chem. Soc., Chem. Commun. 2002, 17, 1856. (e) Pei, W.; Wei, H.-X.; Li, G. J. Chem. Soc., Chem. Commun. 2002, 2412. For the MBH reaction using the combinations of Lewis acids and Lewis bases, see: (f) Uehira, S.; Han, Z.; Shinokubo, H.; Oshima, K. Org. Lett. 1999, 1, 1383. (g) Yagi, K.; Turitani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2002, 4, 3111. (h) Shi, M.; Jiang, J. K.; Cui, S. C.; Feng, Y. S. J. Chem. Soc., Perkin Trans. 1 2001, 390.
27. For the MBH reaction without the direct use of any Lewis bases see: (a) ref 6a. (b) Li, G.; Gao, J.; Wei, H.-X.; Enright, M. Org. Lett. 2000, 2, 617. (c) Basavaiah, D.; Screenivasulu, B.; Rao, J. S. Tetrahedron Lett. 2001, 42, 1147. (d) Pei, W.; Wei, H.-X.; Li, G. J. Chem. Soc., Chem. Commun. 2002, 17, 1856. (e) Pei, W.; Wei, H.-X.; Li, G. J. Chem. Soc., Chem. Commun. 2002, 2412. For the MBH reaction using the combinations of Lewis acids and Lewis bases, see: (f) Uehira, S.; Han, Z.; Shinokubo, H.; Oshima, K. Org. Lett. 1999, 1, 1383. (g) Yagi, K.; Turitani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2002, 4, 3111. (h) Shi, M.; Jiang, J. K.; Cui, S. C.; Feng, Y. S. J. Chem. Soc., Perkin Trans. 1 2001, 390.
28. For the MBH reaction without the direct use of any Lewis bases see: (a) ref 6a. (b) Li, G.; Gao, J.; Wei, H.-X.; Enright, M. Org. Lett. 2000, 2, 617. (c) Basavaiah, D.; Screenivasulu, B.; Rao, J. S. Tetrahedron Lett. 2001, 42, 1147. (d) Pei, W.; Wei, H.-X.; Li, G. J. Chem. Soc., Chem. Commun. 2002, 17, 1856. (e) Pei, W.; Wei, H.-X.; Li, G. J. Chem. Soc., Chem. Commun. 2002, 2412. For the MBH reaction using the combinations of Lewis acids and Lewis bases, see: (f) Uehira, S.; Han, Z.; Shinokubo, H.; Oshima, K. Org. Lett. 1999, 1, 1383. (g) Yagi, K.; Turitani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2002, 4, 3111. (h) Shi, M.; Jiang, J. K.; Cui, S. C.; Feng, Y. S. J. Chem. Soc., Perkin Trans. 1 2001, 390.
29. For the MBH reaction without the direct use of any Lewis bases see: (a) ref 6a. (b) Li, G.; Gao, J.; Wei, H.-X.; Enright, M. Org. Lett. 2000, 2, 617. (c) Basavaiah, D.; Screenivasulu, B.; Rao, J. S. Tetrahedron Lett. 2001, 42, 1147. (d) Pei, W.; Wei, H.-X.; Li, G. J. Chem. Soc., Chem. Commun. 2002, 17, 1856. (e) Pei, W.; Wei, H.-X.; Li, G. J. Chem. Soc., Chem. Commun. 2002, 2412. For the MBH reaction using the combinations of Lewis acids and Lewis bases, see: (f) Uehira, S.; Han, Z.; Shinokubo, H.; Oshima, K. Org. Lett. 1999, 1, 1383. (g) Yagi, K.; Turitani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2002, 4, 3111. (h) Shi, M.; Jiang, J. K.; Cui, S. C.; Feng, Y. S. J. Chem. Soc., Perkin Trans. 1 2001, 390.
30. For the MBH reaction without the direct use of any Lewis bases see: (a) ref 6a. (b) Li, G.; Gao, J.; Wei, H.-X.; Enright, M. Org. Lett. 2000, 2, 617. (c) Basavaiah, D.; Screenivasulu, B.; Rao, J. S. Tetrahedron Lett. 2001, 42, 1147. (d) Pei, W.; Wei, H.-X.; Li, G. J. Chem. Soc., Chem. Commun. 2002, 17, 1856. (e) Pei, W.; Wei, H.-X.; Li, G. J. Chem. Soc., Chem. Commun. 2002, 2412. For the MBH reaction using the combinations of Lewis acids and Lewis bases, see: (f) Uehira, S.; Han, Z.; Shinokubo, H.; Oshima, K. Org. Lett. 1999, 1, 1383. (g) Yagi, K.; Turitani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2002, 4, 3111. (h) Shi, M.; Jiang, J. K.; Cui, S. C.; Feng, Y. S. J. Chem. Soc., Perkin Trans. 1 2001, 390.
31. 2) bond formations: (a) Taniguchi, M.; Hino, T.; Kishi, Y. Tetrahedron Lett. 1986, 27, 4767. (b) Itoh, A.; Pzawa, S.; Oshima, K. ; Nozaki, H. Bull. Chem. Soc. Jpn. 1981, 54, 274.
32. 2) bond formations: (a) Taniguchi, M.; Hino, T.; Kishi, Y. Tetrahedron Lett. 1986, 27, 4767. (b) Itoh, A.; Pzawa, S.; Oshima, K. ; Nozaki, H. Bull. Chem. Soc. Jpn. 1981, 54, 274.
33. 3, 300 MHz): δ 7.51 (d J = 8.1 Hz, 2H), 7.33 m 5H), 7.01 (dd J = 1.5, 7.8 Hz, 2H), 5.45 (dd J = 3.5, 8.6 Hz, 1H), 4.91 (m 2H), 4.70 (dd J = 8.6, 8.6 Hz, 1H), 4.25 dd J = 3.5, 8.9 Hz, 1H), 3.37 (dd J = 9.8, 9.8 Hz, 1H), 3.32 (d J = 8.6 Hz, 1H), 3.23 (d J = 5.1, 9.8 Hz, 1H).
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