In- or In(I)-employed diastereoselective Reformatsky-type reactions with ketones: 1H NMR investigations on the active species

Organic Letters

Volumn 6, Issue 24, 2004, Pages 4475-4478

  Babu, Srinivasarao Arulananda ^a   Yasuda, Makoto ^a   Shibata, Ikuya ^a   Baba, Akio ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALCOHOL DERIVATIVE; CARBON; ESTER DERIVATIVE; HALIDE; HALOALCOHOL; INDIUM;

ARTICLE; COVALENT BOND; DERIVATIZATION; DIASTEREOISOMER; ESTERIFICATION; ISOMER; METALLATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REFORMATSKY REACTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 10044234065     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0482846     Document Type: Article

References (44)

1. Reformatsky, S. Chem. Ber. 1887, 20, 1210.
2. (a) Fürstner. A. Synthesis 1989, 571.
3. (b) Rathke, M. W.; Weipert, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 2, p 277.
4. (a) Rieke, R. D.; Uhm, S. J. Synthesis 1975, 452.
5. (b) Santaniello, E.; Manzocchi, A. Synthesis 1977, 698.
6. (c) Csuk, R.; Fürstner, A.; Weidmann, H. J. Chem. Soc., Chem Commun. 1986, 775.
7. (d) Burkhardt, E.; Rieke, R. D. J. Org. Chem. 1985, 50, 416.
8. (e) Inaba, S.-I.; Rieke, R. D. Tetrahedron Lett. 1985, 26, 155.
9. (f) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904.
10. (g) Moriwake, T. J. Org. Chem. 1966, 31, 983.
11. (h) Borno, A.; Bigley, D. B. J. Chem. Soc., Perkin Trans. 2 1983, 1311.
12. (i) Paresh, J. D.; Shelton, D. R.; Little, R. D. Org. Lett. 2003, 5, 3615.
13. (j) Shibata, I.; Suwa, T.; Sakakibara, H.; Baba, A. Org. Lett. 2002, 4, 301 and references therein.
14. For recent reviews, see: (a) Cintas, P. Synlett 1995, 1087. (b) Podlech, J.; Maier, T. C. Synthesis 2003, 633. (c) Nair, V.; Ros, S.; Jayan, C. N.; Pillai, B.; S. Tetrahedron 2004, 60, 1959. (d) Chan, T. H.; Li, C-J.; Lee, M. C; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181.
15. For recent reviews, see: (a) Cintas, P. Synlett 1995, 1087. (b) Podlech, J.; Maier, T. C. Synthesis 2003, 633. (c) Nair, V.; Ros, S.; Jayan, C. N.; Pillai, B.; S. Tetrahedron 2004, 60, 1959. (d) Chan, T. H.; Li, C-J.; Lee, M. C; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181.
16. For recent reviews, see: (a) Cintas, P. Synlett 1995, 1087. (b) Podlech, J.; Maier, T. C. Synthesis 2003, 633. (c) Nair, V.; Ros, S.; Jayan, C. N.; Pillai, B.; S. Tetrahedron 2004, 60, 1959. (d) Chan, T. H.; Li, C-J.; Lee, M. C; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181.
17. For recent reviews, see: (a) Cintas, P. Synlett 1995, 1087. (b) Podlech, J.; Maier, T. C. Synthesis 2003, 633. (c) Nair, V.; Ros, S.; Jayan, C. N.; Pillai, B.; S. Tetrahedron 2004, 60, 1959. (d) Chan, T. H.; Li, C-J.; Lee, M. C; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181.
18. (a) Kanai, K.; Wakabayashi, H.; Honda, T. Org. Lett. 2000, 2, 2549 and references therein.
19. (b) Aoyagi, Y.; Tanaka, W.; Ohta, A. J. Chem. Soc., Chem. Commun. 1994, 1225.
20. (c) Delaunay, J.; Orliac-Le Moing, A.; Simonet, J. Tetrahedron 1988, 44, 7089.
21. (d) Canceill, J.; Basselier, J. J.; Jacques, J. Bull. Soc. Chim. Fr. 1967, 1024.
22. Ross, N. A.; Bartsch, R. A. J. Org. Chem. 2003, 68, 360 and references therein.
23. For some recent papers, see: (a) Kumar, S. Kaur, P. Tetrahedron Lett. 2004, 45, 3413. (b) Loh, T.-P.; Yin, Z.; Song, H.-S.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 911. (c) Yi, X.-H.; Meng, Y.; Li, C.-J. J. Chem. Soc., Chem. Commun. 1998, 449. (d) Hirashita, T.; Kamei, T.; Satake, M.; Horie, T.; Shimizu, H.; Araki, S. Org. Biomol, Chem. 2003, 1, 3799. (e) Babu, S. A.; Yasuda, M.; Shibata, I., Baba, A. Synlett 2004, 1223. (f) Paquette, L., A. Synthesis 2003, 765.
24. For some recent papers, see: (a) Kumar, S. Kaur, P. Tetrahedron Lett. 2004, 45, 3413. (b) Loh, T.-P.; Yin, Z.; Song, H.-S.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 911. (c) Yi, X.-H.; Meng, Y.; Li, C.-J. J. Chem. Soc., Chem. Commun. 1998, 449. (d) Hirashita, T.; Kamei, T.; Satake, M.; Horie, T.; Shimizu, H.; Araki, S. Org. Biomol, Chem. 2003, 1, 3799. (e) Babu, S. A.; Yasuda, M.; Shibata, I., Baba, A. Synlett 2004, 1223. (f) Paquette, L., A. Synthesis 2003, 765.
25. For some recent papers, see: (a) Kumar, S. Kaur, P. Tetrahedron Lett. 2004, 45, 3413. (b) Loh, T.-P.; Yin, Z.; Song, H.-S.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 911. (c) Yi, X.-H.; Meng, Y.; Li, C.-J. J. Chem. Soc., Chem. Commun. 1998, 449. (d) Hirashita, T.; Kamei, T.; Satake, M.; Horie, T.; Shimizu, H.; Araki, S. Org. Biomol, Chem. 2003, 1, 3799. (e) Babu, S. A.; Yasuda, M.; Shibata, I., Baba, A. Synlett 2004, 1223. (f) Paquette, L., A. Synthesis 2003, 765.
26. For some recent papers, see: (a) Kumar, S. Kaur, P. Tetrahedron Lett. 2004, 45, 3413. (b) Loh, T.-P.; Yin, Z.; Song, H.-S.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 911. (c) Yi, X.-H.; Meng, Y.; Li, C.-J. J. Chem. Soc., Chem. Commun. 1998, 449. (d) Hirashita, T.; Kamei, T.; Satake, M.; Horie, T.; Shimizu, H.; Araki, S. Org. Biomol, Chem. 2003, 1, 3799. (e) Babu, S. A.; Yasuda, M.; Shibata, I., Baba, A. Synlett 2004, 1223. (f) Paquette, L., A. Synthesis 2003, 765.
27. For some recent papers, see: (a) Kumar, S. Kaur, P. Tetrahedron Lett. 2004, 45, 3413. (b) Loh, T.-P.; Yin, Z.; Song, H.-S.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 911. (c) Yi, X.-H.; Meng, Y.; Li, C.-J. J. Chem. Soc., Chem. Commun. 1998, 449. (d) Hirashita, T.; Kamei, T.; Satake, M.; Horie, T.; Shimizu, H.; Araki, S. Org. Biomol, Chem. 2003, 1, 3799. (e) Babu, S. A.; Yasuda, M.; Shibata, I., Baba, A. Synlett 2004, 1223. (f) Paquette, L., A. Synthesis 2003, 765.
28. For some recent papers, see: (a) Kumar, S. Kaur, P. Tetrahedron Lett. 2004, 45, 3413. (b) Loh, T.-P.; Yin, Z.; Song, H.-S.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 911. (c) Yi, X.-H.; Meng, Y.; Li, C.-J. J. Chem. Soc., Chem. Commun. 1998, 449. (d) Hirashita, T.; Kamei, T.; Satake, M.; Horie, T.; Shimizu, H.; Araki, S. Org. Biomol, Chem. 2003, 1, 3799. (e) Babu, S. A.; Yasuda, M.; Shibata, I., Baba, A. Synlett 2004, 1223. (f) Paquette, L., A. Synthesis 2003, 765.
29. For early works dealing with nondiastereoselective Reformatsky-type reactions, see: (a) Chao, L.-C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253. (b) Nair, V.; Jayan, C. N.; Ros, S. Tetrahedron 2001, 57, 9453. (c) Araki, S.; Ito, H.; Butsugan, Y. Synth. Commun. 1988, 18, 453. (d) Araki, S.; Katsumura, N.; Kawasaki, K.-I.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1991, 499. (e) Schick, H.; Ludwig, R.; Schwarz, K.-H.; Kleiner, K.; Kunath, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1191. (f) Araki, S.; Katsumura, N.; Kawasaki, K.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1991, 499. (g) Yi, X.-H.; Meng, Y.; Li, C.-J. Tetrahedron Lett. 1997, 38, 4731.
30. For early works dealing with nondiastereoselective Reformatsky-type reactions, see: (a) Chao, L.-C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253. (b) Nair, V.; Jayan, C. N.; Ros, S. Tetrahedron 2001, 57, 9453. (c) Araki, S.; Ito, H.; Butsugan, Y. Synth. Commun. 1988, 18, 453. (d) Araki, S.; Katsumura, N.; Kawasaki, K.-I.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1991, 499. (e) Schick, H.; Ludwig, R.; Schwarz, K.-H.; Kleiner, K.; Kunath, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1191. (f) Araki, S.; Katsumura, N.; Kawasaki, K.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1991, 499. (g) Yi, X.-H.; Meng, Y.; Li, C.-J. Tetrahedron Lett. 1997, 38, 4731.
31. For early works dealing with nondiastereoselective Reformatsky-type reactions, see: (a) Chao, L.-C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253. (b) Nair, V.; Jayan, C. N.; Ros, S. Tetrahedron 2001, 57, 9453. (c) Araki, S.; Ito, H.; Butsugan, Y. Synth. Commun. 1988, 18, 453. (d) Araki, S.; Katsumura, N.; Kawasaki, K.-I.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1991, 499. (e) Schick, H.; Ludwig, R.; Schwarz, K.-H.; Kleiner, K.; Kunath, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1191. (f) Araki, S.; Katsumura, N.; Kawasaki, K.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1991, 499. (g) Yi, X.-H.; Meng, Y.; Li, C.-J. Tetrahedron Lett. 1997, 38, 4731.
32. For early works dealing with nondiastereoselective Reformatsky-type reactions, see: (a) Chao, L.-C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253. (b) Nair, V.; Jayan, C. N.; Ros, S. Tetrahedron 2001, 57, 9453. (c) Araki, S.; Ito, H.; Butsugan, Y. Synth. Commun. 1988, 18, 453. (d) Araki, S.; Katsumura, N.; Kawasaki, K.-I.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1991, 499. (e) Schick, H.; Ludwig, R.; Schwarz, K.-H.; Kleiner, K.; Kunath, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1191. (f) Araki, S.; Katsumura, N.; Kawasaki, K.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1991, 499. (g) Yi, X.-H.; Meng, Y.; Li, C.-J. Tetrahedron Lett. 1997, 38, 4731.
33. For early works dealing with nondiastereoselective Reformatsky-type reactions, see: (a) Chao, L.-C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253. (b) Nair, V.; Jayan, C. N.; Ros, S. Tetrahedron 2001, 57, 9453. (c) Araki, S.; Ito, H.; Butsugan, Y. Synth. Commun. 1988, 18, 453. (d) Araki, S.; Katsumura, N.; Kawasaki, K.-I.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1991, 499. (e) Schick, H.; Ludwig, R.; Schwarz, K.-H.; Kleiner, K.; Kunath, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1191. (f) Araki, S.; Katsumura, N.; Kawasaki, K.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1991, 499. (g) Yi, X.-H.; Meng, Y.; Li, C.-J. Tetrahedron Lett. 1997, 38, 4731.
34. For early works dealing with nondiastereoselective Reformatsky-type reactions, see: (a) Chao, L.-C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253. (b) Nair, V.; Jayan, C. N.; Ros, S. Tetrahedron 2001, 57, 9453. (c) Araki, S.; Ito, H.; Butsugan, Y. Synth. Commun. 1988, 18, 453. (d) Araki, S.; Katsumura, N.; Kawasaki, K.-I.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1991, 499. (e) Schick, H.; Ludwig, R.; Schwarz, K.-H.; Kleiner, K.; Kunath, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1191. (f) Araki, S.; Katsumura, N.; Kawasaki, K.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1991, 499. (g) Yi, X.-H.; Meng, Y.; Li, C.-J. Tetrahedron Lett. 1997, 38, 4731.
35. For early works dealing with nondiastereoselective Reformatsky-type reactions, see: (a) Chao, L.-C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253. (b) Nair, V.; Jayan, C. N.; Ros, S. Tetrahedron 2001, 57, 9453. (c) Araki, S.; Ito, H.; Butsugan, Y. Synth. Commun. 1988, 18, 453. (d) Araki, S.; Katsumura, N.; Kawasaki, K.-I.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1991, 499. (e) Schick, H.; Ludwig, R.; Schwarz, K.-H.; Kleiner, K.; Kunath, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1191. (f) Araki, S.; Katsumura, N.; Kawasaki, K.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1991, 499. (g) Yi, X.-H.; Meng, Y.; Li, C.-J. Tetrahedron Lett. 1997, 38, 4731.
36. (a) With respect to yields and diastereoselection, In and InBr afforded a similar trend. But InCl and InI furnished relatively a moderate selectivity. One of the reasons might be that dissimilar halide ions react with the α-bromo ester to form the active enolates.
37. (b) Vedejs, E.; Daugulis, O. J. Org. Chem. 1996, 61, 5702.
38. 1 (anti isomers).
39. 1H NMR spectrum revealed the formation of anti/syn isomers of the respective alcohols (Figure 5b). (
40. 1H NMR spectral region.
41. (a) In a different experiment, when the reaction mixture was left overnight, only methyl propionate was observed.
42. 2-COOEt did not afford any new signal.
43. 1H NMR studies on allyl indium cases, see: (a) Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228. (b) Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831.
44. 1H NMR studies on allyl indium cases, see: (a) Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228. (b) Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831.