Enantioselective [2,3]-Wittig rearrangement induced by asymmetric lithiation with a t-butyllithium / chiral bis(oxazoline) system

Tetrahedron Letters

Volumn 39, Issue 31, 1998, Pages 5513-5516

  Tomooka, Katsuhiko ^a   Komine, Nobuyuki ^a   Nakai, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; LIGAND; LITHIUM DERIVATIVE; OXAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; METHODOLOGY; STEREOCHEMISTRY;

EID: 0032581664     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01086-7     Document Type: Article

References (27)

1. 1. Reviews : (a) Marshall, J. A. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M.; Fleming, I., Ed.; Pergamon: New York, 1991; p 975-1014.
2. (b) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105-209;
3. (c) Nakai, T.; Tomooka, K. Pure and Appl. Chem. 1997, 69, 595-600.
4. 2. For the first example of the enantio-selective version of this rearrangement, see: Marshall, J. A.; Lebreton, J. J. Am. Chem. Soc. 1988, 110, 2925-2931. For the examples involving a chiral boron enolate, see; Fujimoto, K.; Nakai, T. Tetrahedron Lett. 1994, 35, 5019-5022; Fujimoto, K.; Matsuhashi, C.; Nakai, T. Heterocydes, 1996, 42, 423-435. For the recent example, see: Susan E. G.; Peter H.; Gary R. J. Chem. Commun., 1998, 123-124.
5. 2. For the first example of the enantio-selective version of this rearrangement, see: Marshall, J. A.; Lebreton, J. J. Am. Chem. Soc. 1988, 110, 2925-2931. For the examples involving a chiral boron enolate, see; Fujimoto, K.; Nakai, T. Tetrahedron Lett. 1994, 35, 5019-5022; Fujimoto, K.; Matsuhashi, C.; Nakai, T. Heterocydes, 1996, 42, 423-435. For the recent example, see: Susan E. G.; Peter H.; Gary R. J. Chem. Commun., 1998, 123-124.
6. 2. For the first example of the enantio-selective version of this rearrangement, see: Marshall, J. A.; Lebreton, J. J. Am. Chem. Soc. 1988, 110, 2925-2931. For the examples involving a chiral boron enolate, see; Fujimoto, K.; Nakai, T. Tetrahedron Lett. 1994, 35, 5019-5022; Fujimoto, K.; Matsuhashi, C.; Nakai, T. Heterocydes, 1996, 42, 423-435. For the recent example, see: Susan E. G.; Peter H.; Gary R. J. Chem. Commun., 1998, 123-124.
7. 2. For the first example of the enantio-selective version of this rearrangement, see: Marshall, J. A.; Lebreton, J. J. Am. Chem. Soc. 1988, 110, 2925-2931. For the examples involving a chiral boron enolate, see; Fujimoto, K.; Nakai, T. Tetrahedron Lett. 1994, 35, 5019-5022; Fujimoto, K.; Matsuhashi, C.; Nakai, T. Heterocydes, 1996, 42, 423-435. For the recent example, see: Susan E. G.; Peter H.; Gary R. J. Chem. Commun., 1998, 123-124.
8. 3. Reviews: (a) Hoppe, D.; Hense, T. Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316.
9. (b) Beak, P.; Basu, A.; Gallageher , D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-560.
10. 4. Kang, J.; Cho, W. O.; Cho, H. G.; Oh, H. J. Bull. Korean. Chem. Soc. 1994, 15, 732-739. They have also reported that the rearrangement of (Z)-cinnamyl propargyl ether with s-BuLi / 2 gives the erythro-product with 71% ee and 48% de.
11. 5. This work was presented at the Annual Meeting of the Chemical Society of Japan, March, 1996, Abstrc. 3H435.
12. 6. After the completion of this work, Manabe has reported that the use of the chiral amino ether as ECL provides up to 80% ee in the n-BuLi-induced rearrangements of bis-propargyl ether or crotyl benzyl ether: Manabe, S. J. Chem. Soc., Chem. Commun. 1997, 737-738.
13. 7. Reviews on chiral bis(oxazoline)-mediated asymmetric reactions: (a) Bolm, C. Angew. Chem. Int. Ed. Engl. 1991, 30, 542-543.
14. (b) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339-345.
15. (c) Reiser, O. Angew. Chem. Int. Ed. Engl. 1993, 32, 547-549. For the use of chiral bis(oxazoline) / alkyllithium complexes in the asymmetric addition reaction to imines, see: Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797-8798. Quite recently, Hodgson's group has reported the enantioselective rearrangement reaction of epoxides induced with a chiral bis(oxazoline) / alkyllithium system: Hodgson, D. M.; Lee, G. P. Tetrahedron Asymmetry, 1997, 8, 2303-2306.
16. (c) Reiser, O. Angew. Chem. Int. Ed. Engl. 1993, 32, 547-549. For the use of chiral bis(oxazoline) / alkyllithium complexes in the asymmetric addition reaction to imines, see: Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797-8798. Quite recently, Hodgson's group has reported the enantioselective rearrangement reaction of epoxides induced with a chiral bis(oxazoline) / alkyllithium system: Hodgson, D. M.; Lee, G. P. Tetrahedron Asymmetry, 1997, 8, 2303-2306.
17. (c) Reiser, O. Angew. Chem. Int. Ed. Engl. 1993, 32, 547-549. For the use of chiral bis(oxazoline) / alkyllithium complexes in the asymmetric addition reaction to imines, see: Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797-8798. Quite recently, Hodgson's group has reported the enantioselective rearrangement reaction of epoxides induced with a chiral bis(oxazoline) / alkyllithium system: Hodgson, D. M.; Lee, G. P. Tetrahedron Asymmetry, 1997, 8, 2303-2306.
18. 8. For the diastereoselectivity of this variant, see: Mikami, K.; Kimura, Y.; Kishi, N.; Nakai, T. J. Org. Chem. 1983, 48, 279-280, and references cited therein.
19. 9. Chiral bisoxazoline (S,S)-3 was prepared by the literature method: Denmark, S. E.; Nakajima, N.; Nicaise, O. J. -C.; Faucher, A. M.; Edwards, J. P. J. Org. Chem. 1995, 60, 4884-4892.
20. 3): Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339-6348.
21. 11. It is worth noting that (S,S)-3 was recovered in 80% yield.
22. 12. For the diastereoselectivity of these variants, see: Nakai, T.; Mikami, K.; Taya, S.; Fujita, Y.; J. Am. Chem. Soc. 1981, 103, 6492-6494; Mikami, K.; Azuma, K; Nakai, T. Tetrahedron, 1984, 2303-2308.
23. 12. For the diastereoselectivity of these variants, see: Nakai, T.; Mikami, K.; Taya, S.; Fujita, Y.; J. Am. Chem. Soc. 1981, 103, 6492-6494; Mikami, K.; Azuma, K; Nakai, T. Tetrahedron, 1984, 2303-2308.
24. 13. Furthermore, we found that the rearrangement of (Z)-cinnamyl γ-(trimethylsilyl)propargyl ether with t-BuLi / (S,S)-3 afforded the threo-product with 73% ee and 10% de.
25. 1H NMR analysis of the MTPA esters.
26. 15. The absolute configurations of threo and erythro-7 were determined by the modified Mosher method: Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
27. 16. Similar mechanistic studies of asymmetric lithiations using a racemic deuterated substrate have been reported: Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715-721.