Asymmetric synthesis of allyl- and α-allenylamines from chiral imines and alkynes via (η2-imine)Ti(O-i-Pr)2 complexes

Organic Letters

Volumn 5, Issue 12, 2003, Pages 2145-2148

  Fukuhara, Kohki ^a   Okamoto, Sentaro ^a,b   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b KANAGAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKYNE DERIVATIVE; ALLYL COMPOUND; AMINE; IMINE; O METHYLPHENYLGLYCINOL; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0141786838     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034599u     Document Type: Article

References (26)

1. For a review on methods for synthesis of allylamines, see: Johannsen, M. ; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689. See also ref 3.
2. For recent leading references, see: (a) Billet, M.; Schoenfelder, A.; Klotz, P.; Mann, A. Tetrahedron Lett. 2002, 43, 1453. (b) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855. (c) Ohno, H.; Anzai, M.; Toda, A.; Ohishi, S.; Fujii, N.; Tanaka, T.; Takemoto, Y.; Ibuka, T. J. Org. Chem. 2001, 66, 4904.
3. For recent leading references, see: (a) Billet, M.; Schoenfelder, A.; Klotz, P.; Mann, A. Tetrahedron Lett. 2002, 43, 1453. (b) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855. (c) Ohno, H.; Anzai, M.; Toda, A.; Ohishi, S.; Fujii, N.; Tanaka, T.; Takemoto, Y.; Ibuka, T. J. Org. Chem. 2001, 66, 4904.
4. For recent leading references, see: (a) Billet, M.; Schoenfelder, A.; Klotz, P.; Mann, A. Tetrahedron Lett. 2002, 43, 1453. (b) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855. (c) Ohno, H.; Anzai, M.; Toda, A.; Ohishi, S.; Fujii, N.; Tanaka, T.; Takemoto, Y.; Ibuka, T. J. Org. Chem. 2001, 66, 4904.
5. For recent leading references, see: (a) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (b) Chen, Y. K.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 12225. (c) Konno, T.; Nagata, K.; Ishihara, T.; Yamanaka, H. J. Org. Chem. 2002, 67, 1768. (d) Martín, R.; Alcón. M.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2002, 67, 6896. (e) Wipf, P. ; Nunes, R. L.; Ribe, S. Helv. Chim. Acta 2002, 85, 3478. (f) Evans, P. A.; Robinson, J. E.; Moffett, K. K. Org. Lett. 2001, 3, 3269. (g) Löber, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366. (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847. (i) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. (j) Chao, B.; Dittmer, D. C. Tetrahedron Lett. 2001, 42, 5789. (k) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Synlett 2001, 1608.
6. For recent leading references, see: (a) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (b) Chen, Y. K.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 12225. (c) Konno, T.; Nagata, K.; Ishihara, T.; Yamanaka, H. J. Org. Chem. 2002, 67, 1768. (d) Martín, R.; Alcón. M.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2002, 67, 6896. (e) Wipf, P. ; Nunes, R. L.; Ribe, S. Helv. Chim. Acta 2002, 85, 3478. (f) Evans, P. A.; Robinson, J. E.; Moffett, K. K. Org. Lett. 2001, 3, 3269. (g) Löber, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366. (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847. (i) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. (j) Chao, B.; Dittmer, D. C. Tetrahedron Lett. 2001, 42, 5789. (k) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Synlett 2001, 1608.
7. For recent leading references, see: (a) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (b) Chen, Y. K.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 12225. (c) Konno, T.; Nagata, K.; Ishihara, T.; Yamanaka, H. J. Org. Chem. 2002, 67, 1768. (d) Martín, R.; Alcón. M.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2002, 67, 6896. (e) Wipf, P. ; Nunes, R. L.; Ribe, S. Helv. Chim. Acta 2002, 85, 3478. (f) Evans, P. A.; Robinson, J. E.; Moffett, K. K. Org. Lett. 2001, 3, 3269. (g) Löber, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366. (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847. (i) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. (j) Chao, B.; Dittmer, D. C. Tetrahedron Lett. 2001, 42, 5789. (k) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Synlett 2001, 1608.
8. For recent leading references, see: (a) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (b) Chen, Y. K.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 12225. (c) Konno, T.; Nagata, K.; Ishihara, T.; Yamanaka, H. J. Org. Chem. 2002, 67, 1768. (d) Martín, R.; Alcón. M.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2002, 67, 6896. (e) Wipf, P. ; Nunes, R. L.; Ribe, S. Helv. Chim. Acta 2002, 85, 3478. (f) Evans, P. A.; Robinson, J. E.; Moffett, K. K. Org. Lett. 2001, 3, 3269. (g) Löber, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366. (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847. (i) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. (j) Chao, B.; Dittmer, D. C. Tetrahedron Lett. 2001, 42, 5789. (k) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Synlett 2001, 1608.
9. For recent leading references, see: (a) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (b) Chen, Y. K.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 12225. (c) Konno, T.; Nagata, K.; Ishihara, T.; Yamanaka, H. J. Org. Chem. 2002, 67, 1768. (d) Martín, R.; Alcón. M.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2002, 67, 6896. (e) Wipf, P. ; Nunes, R. L.; Ribe, S. Helv. Chim. Acta 2002, 85, 3478. (f) Evans, P. A.; Robinson, J. E.; Moffett, K. K. Org. Lett. 2001, 3, 3269. (g) Löber, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366. (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847. (i) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. (j) Chao, B.; Dittmer, D. C. Tetrahedron Lett. 2001, 42, 5789. (k) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Synlett 2001, 1608.
10. For recent leading references, see: (a) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (b) Chen, Y. K.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 12225. (c) Konno, T.; Nagata, K.; Ishihara, T.; Yamanaka, H. J. Org. Chem. 2002, 67, 1768. (d) Martín, R.; Alcón. M.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2002, 67, 6896. (e) Wipf, P. ; Nunes, R. L.; Ribe, S. Helv. Chim. Acta 2002, 85, 3478. (f) Evans, P. A.; Robinson, J. E.; Moffett, K. K. Org. Lett. 2001, 3, 3269. (g) Löber, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366. (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847. (i) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. (j) Chao, B.; Dittmer, D. C. Tetrahedron Lett. 2001, 42, 5789. (k) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Synlett 2001, 1608.
11. For recent leading references, see: (a) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (b) Chen, Y. K.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 12225. (c) Konno, T.; Nagata, K.; Ishihara, T.; Yamanaka, H. J. Org. Chem. 2002, 67, 1768. (d) Martín, R.; Alcón. M.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2002, 67, 6896. (e) Wipf, P. ; Nunes, R. L.; Ribe, S. Helv. Chim. Acta 2002, 85, 3478. (f) Evans, P. A.; Robinson, J. E.; Moffett, K. K. Org. Lett. 2001, 3, 3269. (g) Löber, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366. (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847. (i) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. (j) Chao, B.; Dittmer, D. C. Tetrahedron Lett. 2001, 42, 5789. (k) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Synlett 2001, 1608.
12. For recent leading references, see: (a) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (b) Chen, Y. K.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 12225. (c) Konno, T.; Nagata, K.; Ishihara, T.; Yamanaka, H. J. Org. Chem. 2002, 67, 1768. (d) Martín, R.; Alcón. M.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2002, 67, 6896. (e) Wipf, P. ; Nunes, R. L.; Ribe, S. Helv. Chim. Acta 2002, 85, 3478. (f) Evans, P. A.; Robinson, J. E.; Moffett, K. K. Org. Lett. 2001, 3, 3269. (g) Löber, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366. (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847. (i) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. (j) Chao, B.; Dittmer, D. C. Tetrahedron Lett. 2001, 42, 5789. (k) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Synlett 2001, 1608.
13. For recent leading references, see: (a) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (b) Chen, Y. K.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 12225. (c) Konno, T.; Nagata, K.; Ishihara, T.; Yamanaka, H. J. Org. Chem. 2002, 67, 1768. (d) Martín, R.; Alcón. M.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2002, 67, 6896. (e) Wipf, P. ; Nunes, R. L.; Ribe, S. Helv. Chim. Acta 2002, 85, 3478. (f) Evans, P. A.; Robinson, J. E.; Moffett, K. K. Org. Lett. 2001, 3, 3269. (g) Löber, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366. (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847. (i) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. (j) Chao, B.; Dittmer, D. C. Tetrahedron Lett. 2001, 42, 5789. (k) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Synlett 2001, 1608.
14. For recent leading references, see: (a) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (b) Chen, Y. K.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 12225. (c) Konno, T.; Nagata, K.; Ishihara, T.; Yamanaka, H. J. Org. Chem. 2002, 67, 1768. (d) Martín, R.; Alcón. M.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2002, 67, 6896. (e) Wipf, P. ; Nunes, R. L.; Ribe, S. Helv. Chim. Acta 2002, 85, 3478. (f) Evans, P. A.; Robinson, J. E.; Moffett, K. K. Org. Lett. 2001, 3, 3269. (g) Löber, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366. (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847. (i) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. (j) Chao, B.; Dittmer, D. C. Tetrahedron Lett. 2001, 42, 5789. (k) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Synlett 2001, 1608.
15. For recent leading references, see: (a) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (b) Chen, Y. K.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 12225. (c) Konno, T.; Nagata, K.; Ishihara, T.; Yamanaka, H. J. Org. Chem. 2002, 67, 1768. (d) Martín, R.; Alcón. M.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2002, 67, 6896. (e) Wipf, P. ; Nunes, R. L.; Ribe, S. Helv. Chim. Acta 2002, 85, 3478. (f) Evans, P. A.; Robinson, J. E.; Moffett, K. K. Org. Lett. 2001, 3, 3269. (g) Löber, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366. (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847. (i) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. (j) Chao, B.; Dittmer, D. C. Tetrahedron Lett. 2001, 42, 5789. (k) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Synlett 2001, 1608.
16. Gao, Y.; Yoshida, Y.; Sato, F. Synlett 1997, 1353.
17. 2 complexes derived from 1 and internal alkynes react with imines to provide the corresponding β,γ-disubstituted allylamines: Gao, Y.; Harada, K.; Sato, F. Tetrahedron Lett. 1995, 36, 5913.
18. 4/2 i-PrMgCl: Sato, F.; Urabe, H. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 319-354. Sato, F.; Okamoto, S. Adv. Synth. Catal. 2001, 343, 759. Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835.
19. 4/2 i-PrMgCl: Sato, F.; Urabe, H. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 319-354. Sato, F.; Okamoto, S. Adv. Synth. Catal. 2001, 343, 759. Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835.
20. 4/2 i-PrMgCl: Sato, F.; Urabe, H. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 319-354. Sato, F.; Okamoto, S. Adv. Synth. Catal. 2001, 343, 759. Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835.
21. 4
22. Ito, H.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 1992, 33, 4469.
23. 2 and amines with alkynes was reported: Grossman, R. B.; Davis, W. M.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 2321.
24. Kawakami, T.; Ohtake, H.; Arakawa, H.; Okachi, T.; Imada, Y.; Murahashi, S. Bull. Chem. Soc. Jpn. 2000, 73, 2423.
25. Yamamoto, Y.; Shimoda, H.; Oda, J.; Inoue, Y. Bull. Chem. Soc. Jpn. 1976, 49, 3247.
26. 8,9