The ester dienolate [2,3]-Wittig rearrangement. Diastereoselective synthesis of 2,3-dialkenyl-substituted 2-hydroxy-γ-lactones

Tetrahedron

Volumn 55, Issue 9, 1999, Pages 2625-2638

  Hiersemann, Martin ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENYL GROUP; ESTER; GAMMA LACTONE DERIVATIVE; METAL DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033605301     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00019-8     Document Type: Article

References (45)

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3. (a) Kallmerten, J. in Houben-weyl, Methods Of Organic Chemistry; Eds.: Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E.; Thieme Verlag Stuttgart 1995, Vol. E 21d, 3757. (b) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105. (c) Brückner, R. in Comprehensive Organic Synthesis; Eds: Trost, B. M.; Flemming, I.; Winterfeldt, E.; Pergamon Press Oxford 1991, Vol. 6, 873. (d) Marshall, J. A. in Comprehensive Organic Synthesis; Eds: Trost, B. M.; Flemming, I.; Pergamon Press Oxford 1991, Vol. 3, 975. (e) Brückner, R. Nachr. Chem. Tech. Lab. 1990, 38, 1506. (f) Mikami, K.; Nakai, T. Synthesis 1991, 594. (h) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885. (g) Schöllkopf, U. Angew. Chem. Int. Engl. Ed. 1970, 9, 763.
4. (a) Kallmerten, J. in Houben-weyl, Methods Of Organic Chemistry; Eds.: Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E.; Thieme Verlag Stuttgart 1995, Vol. E 21d, 3757. (b) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105. (c) Brückner, R. in Comprehensive Organic Synthesis; Eds: Trost, B. M.; Flemming, I.; Winterfeldt, E.; Pergamon Press Oxford 1991, Vol. 6, 873. (d) Marshall, J. A. in Comprehensive Organic Synthesis; Eds: Trost, B. M.; Flemming, I.; Pergamon Press Oxford 1991, Vol. 3, 975. (e) Brückner, R. Nachr. Chem. Tech. Lab. 1990, 38, 1506. (f) Mikami, K.; Nakai, T. Synthesis 1991, 594. (h) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885. (g) Schöllkopf, U. Angew. Chem. Int. Engl. Ed. 1970, 9, 763.
5. (a) Kallmerten, J. in Houben-weyl, Methods Of Organic Chemistry; Eds.: Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E.; Thieme Verlag Stuttgart 1995, Vol. E 21d, 3757. (b) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105. (c) Brückner, R. in Comprehensive Organic Synthesis; Eds: Trost, B. M.; Flemming, I.; Winterfeldt, E.; Pergamon Press Oxford 1991, Vol. 6, 873. (d) Marshall, J. A. in Comprehensive Organic Synthesis; Eds: Trost, B. M.; Flemming, I.; Pergamon Press Oxford 1991, Vol. 3, 975. (e) Brückner, R. Nachr. Chem. Tech. Lab. 1990, 38, 1506. (f) Mikami, K.; Nakai, T. Synthesis 1991, 594. (h) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885. (g) Schöllkopf, U. Angew. Chem. Int. Engl. Ed. 1970, 9, 763.
6. (a) Kallmerten, J. in Houben-weyl, Methods Of Organic Chemistry; Eds.: Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E.; Thieme Verlag Stuttgart 1995, Vol. E 21d, 3757. (b) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105. (c) Brückner, R. in Comprehensive Organic Synthesis; Eds: Trost, B. M.; Flemming, I.; Winterfeldt, E.; Pergamon Press Oxford 1991, Vol. 6, 873. (d) Marshall, J. A. in Comprehensive Organic Synthesis; Eds: Trost, B. M.; Flemming, I.; Pergamon Press Oxford 1991, Vol. 3, 975. (e) Brückner, R. Nachr. Chem. Tech. Lab. 1990, 38, 1506. (f) Mikami, K.; Nakai, T. Synthesis 1991, 594. (h) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885. (g) Schöllkopf, U. Angew. Chem. Int. Engl. Ed. 1970, 9, 763.
7. (a) Kallmerten, J. in Houben-weyl, Methods Of Organic Chemistry; Eds.: Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E.; Thieme Verlag Stuttgart 1995, Vol. E 21d, 3757. (b) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105. (c) Brückner, R. in Comprehensive Organic Synthesis; Eds: Trost, B. M.; Flemming, I.; Winterfeldt, E.; Pergamon Press Oxford 1991, Vol. 6, 873. (d) Marshall, J. A. in Comprehensive Organic Synthesis; Eds: Trost, B. M.; Flemming, I.; Pergamon Press Oxford 1991, Vol. 3, 975. (e) Brückner, R. Nachr. Chem. Tech. Lab. 1990, 38, 1506. (f) Mikami, K.; Nakai, T. Synthesis 1991, 594. (h) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885. (g) Schöllkopf, U. Angew. Chem. Int. Engl. Ed. 1970, 9, 763.
8. (a) Kallmerten, J. in Houben-weyl, Methods Of Organic Chemistry; Eds.: Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E.; Thieme Verlag Stuttgart 1995, Vol. E 21d, 3757. (b) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105. (c) Brückner, R. in Comprehensive Organic Synthesis; Eds: Trost, B. M.; Flemming, I.; Winterfeldt, E.; Pergamon Press Oxford 1991, Vol. 6, 873. (d) Marshall, J. A. in Comprehensive Organic Synthesis; Eds: Trost, B. M.; Flemming, I.; Pergamon Press Oxford 1991, Vol. 3, 975. (e) Brückner, R. Nachr. Chem. Tech. Lab. 1990, 38, 1506. (f) Mikami, K.; Nakai, T. Synthesis 1991, 594. (h) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885. (g) Schöllkopf, U. Angew. Chem. Int. Engl. Ed. 1970, 9, 763.
9. (a) Kallmerten, J. in Houben-weyl, Methods Of Organic Chemistry; Eds.: Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E.; Thieme Verlag Stuttgart 1995, Vol. E 21d, 3757. (b) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105. (c) Brückner, R. in Comprehensive Organic Synthesis; Eds: Trost, B. M.; Flemming, I.; Winterfeldt, E.; Pergamon Press Oxford 1991, Vol. 6, 873. (d) Marshall, J. A. in Comprehensive Organic Synthesis; Eds: Trost, B. M.; Flemming, I.; Pergamon Press Oxford 1991, Vol. 3, 975. (e) Brückner, R. Nachr. Chem. Tech. Lab. 1990, 38, 1506. (f) Mikami, K.; Nakai, T. Synthesis 1991, 594. (h) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885. (g) Schöllkopf, U. Angew. Chem. Int. Engl. Ed. 1970, 9, 763.
10. (a) Kallmerten, J. in Houben-weyl, Methods Of Organic Chemistry; Eds.: Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E.; Thieme Verlag Stuttgart 1995, Vol. E 21d, 3757. (b) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105. (c) Brückner, R. in Comprehensive Organic Synthesis; Eds: Trost, B. M.; Flemming, I.; Winterfeldt, E.; Pergamon Press Oxford 1991, Vol. 6, 873. (d) Marshall, J. A. in Comprehensive Organic Synthesis; Eds: Trost, B. M.; Flemming, I.; Pergamon Press Oxford 1991, Vol. 3, 975. (e) Brückner, R. Nachr. Chem. Tech. Lab. 1990, 38, 1506. (f) Mikami, K.; Nakai, T. Synthesis 1991, 594. (h) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885. (g) Schöllkopf, U. Angew. Chem. Int. Engl. Ed. 1970, 9, 763.
11. For asymmetric amide enolate [2,3]-Wittig rearrangements, see (a) Mikami, K.; Takahashi, O.; Kasuga, T.; Nakai, T Chem. Lett. 1985, 1729. (b) Uchikawa, M.; Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 4577. (c) Kress, M. H.; Yang, C.; Yasuda, N.; Grabowski, E. J. J. Tetrahedron Lett. 1997, 38, 2633.
12. For asymmetric amide enolate [2,3]-Wittig rearrangements, see (a) Mikami, K.; Takahashi, O.; Kasuga, T.; Nakai, T Chem. Lett. 1985, 1729. (b) Uchikawa, M.; Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 4577. (c) Kress, M. H.; Yang, C.; Yasuda, N.; Grabowski, E. J. J. Tetrahedron Lett. 1997, 38, 2633.
13. For asymmetric amide enolate [2,3]-Wittig rearrangements, see (a) Mikami, K.; Takahashi, O.; Kasuga, T.; Nakai, T Chem. Lett. 1985, 1729. (b) Uchikawa, M.; Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 4577. (c) Kress, M. H.; Yang, C.; Yasuda, N.; Grabowski, E. J. J. Tetrahedron Lett. 1997, 38, 2633.
14. For asymmetric oxazoline azaenolate [2,3]-Wittig rearrangements, see (a) Mikami, K.; Fujimoto, K.; Kasuga, T.; Nakai, T. Tetrahedron Lett. 1984, 25, 6011. (b) Mikami, K.; Kasuga, T.; Fujimoto, K.; Nakai, T. Tetrahedron Lett. 1986, 27, 4185.
15. For asymmetric oxazoline azaenolate [2,3]-Wittig rearrangements, see (a) Mikami, K.; Fujimoto, K.; Kasuga, T.; Nakai, T. Tetrahedron Lett. 1984, 25, 6011. (b) Mikami, K.; Kasuga, T.; Fujimoto, K.; Nakai, T. Tetrahedron Lett. 1986, 27, 4185.
16. For an asymmetric hydrazone azaenolate [2,3]-Wittig rearrangement, see Enders, D.; Backhaus, D.; Runsink, J. Angew. Chem. Int. Engl. Ed. 1994, 33, 2098.
17. Takhashi, O.; Mikami, K.; Nakai, T. Chem. Lett. 1987, 69.
18. (a) Takahashi, O.; Maeda, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1355. (b) Takahashi, O.; Saka, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1599. (c) Uchikawa, M.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 4581. (d) Kuroda, S.; Katsuki, T. Yamaguchi, M. Tetrahedron Lett. 1987, 28, 803. (e) Kuroda, S.; Sakaguchi, S.; Ikegami, S.; Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1988, 29, 4763. (f) Brückner, R. Chem. Ber. 1989, 122, 703. (g) Mikami, K.; Takahashi, O.; Fujimoto, K.; Nakai, T. Synlett 1991, 629. (h) Oh, T.; Wrobel, Z.; Rubenstein, S. M. Tetrahedron Lett. 1991, 32, 4647. Marshall, J. A.; Wang, X. J. Org. Chem. 1991, 56, 4913. (i) Okamura, H.; Kuroda, S.; Ikegami, S.; Tomita, K.; Sugimoto, Y.; Sakaguchi, S.; Ito, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedron 1993, 49, 10531. (j) Fujimoto, K.; Nakai, T. Tetrahedron Lett. 1994, 35, 5019. (k) Reetz, M. T.; Griebenow, N.; Goddard, R. J. Chem. Soc. Chem. Commun. 1995, 1605. (l) Konno, T.; Umetani, H.; Kitazume, T. J. Org. Chem. 1997, 62, 137.
19. (a) Takahashi, O.; Maeda, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1355. (b) Takahashi, O.; Saka, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1599. (c) Uchikawa, M.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 4581. (d) Kuroda, S.; Katsuki, T. Yamaguchi, M. Tetrahedron Lett. 1987, 28, 803. (e) Kuroda, S.; Sakaguchi, S.; Ikegami, S.; Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1988, 29, 4763. (f) Brückner, R. Chem. Ber. 1989, 122, 703. (g) Mikami, K.; Takahashi, O.; Fujimoto, K.; Nakai, T. Synlett 1991, 629. (h) Oh, T.; Wrobel, Z.; Rubenstein, S. M. Tetrahedron Lett. 1991, 32, 4647. Marshall, J. A.; Wang, X. J. Org. Chem. 1991, 56, 4913. (i) Okamura, H.; Kuroda, S.; Ikegami, S.; Tomita, K.; Sugimoto, Y.; Sakaguchi, S.; Ito, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedron 1993, 49, 10531. (j) Fujimoto, K.; Nakai, T. Tetrahedron Lett. 1994, 35, 5019. (k) Reetz, M. T.; Griebenow, N.; Goddard, R. J. Chem. Soc. Chem. Commun. 1995, 1605. (l) Konno, T.; Umetani, H.; Kitazume, T. J. Org. Chem. 1997, 62, 137.
20. (a) Takahashi, O.; Maeda, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1355. (b) Takahashi, O.; Saka, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1599. (c) Uchikawa, M.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 4581. (d) Kuroda, S.; Katsuki, T. Yamaguchi, M. Tetrahedron Lett. 1987, 28, 803. (e) Kuroda, S.; Sakaguchi, S.; Ikegami, S.; Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1988, 29, 4763. (f) Brückner, R. Chem. Ber. 1989, 122, 703. (g) Mikami, K.; Takahashi, O.; Fujimoto, K.; Nakai, T. Synlett 1991, 629. (h) Oh, T.; Wrobel, Z.; Rubenstein, S. M. Tetrahedron Lett. 1991, 32, 4647. Marshall, J. A.; Wang, X. J. Org. Chem. 1991, 56, 4913. (i) Okamura, H.; Kuroda, S.; Ikegami, S.; Tomita, K.; Sugimoto, Y.; Sakaguchi, S.; Ito, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedron 1993, 49, 10531. (j) Fujimoto, K.; Nakai, T. Tetrahedron Lett. 1994, 35, 5019. (k) Reetz, M. T.; Griebenow, N.; Goddard, R. J. Chem. Soc. Chem. Commun. 1995, 1605. (l) Konno, T.; Umetani, H.; Kitazume, T. J. Org. Chem. 1997, 62, 137.
21. (a) Takahashi, O.; Maeda, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1355. (b) Takahashi, O.; Saka, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1599. (c) Uchikawa, M.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 4581. (d) Kuroda, S.; Katsuki, T. Yamaguchi, M. Tetrahedron Lett. 1987, 28, 803. (e) Kuroda, S.; Sakaguchi, S.; Ikegami, S.; Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1988, 29, 4763. (f) Brückner, R. Chem. Ber. 1989, 122, 703. (g) Mikami, K.; Takahashi, O.; Fujimoto, K.; Nakai, T. Synlett 1991, 629. (h) Oh, T.; Wrobel, Z.; Rubenstein, S. M. Tetrahedron Lett. 1991, 32, 4647. Marshall, J. A.; Wang, X. J. Org. Chem. 1991, 56, 4913. (i) Okamura, H.; Kuroda, S.; Ikegami, S.; Tomita, K.; Sugimoto, Y.; Sakaguchi, S.; Ito, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedron 1993, 49, 10531. (j) Fujimoto, K.; Nakai, T. Tetrahedron Lett. 1994, 35, 5019. (k) Reetz, M. T.; Griebenow, N.; Goddard, R. J. Chem. Soc. Chem. Commun. 1995, 1605. (l) Konno, T.; Umetani, H.; Kitazume, T. J. Org. Chem. 1997, 62, 137.
22. (a) Takahashi, O.; Maeda, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1355. (b) Takahashi, O.; Saka, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1599. (c) Uchikawa, M.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 4581. (d) Kuroda, S.; Katsuki, T. Yamaguchi, M. Tetrahedron Lett. 1987, 28, 803. (e) Kuroda, S.; Sakaguchi, S.; Ikegami, S.; Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1988, 29, 4763. (f) Brückner, R. Chem. Ber. 1989, 122, 703. (g) Mikami, K.; Takahashi, O.; Fujimoto, K.; Nakai, T. Synlett 1991, 629. (h) Oh, T.; Wrobel, Z.; Rubenstein, S. M. Tetrahedron Lett. 1991, 32, 4647. Marshall, J. A.; Wang, X. J. Org. Chem. 1991, 56, 4913. (i) Okamura, H.; Kuroda, S.; Ikegami, S.; Tomita, K.; Sugimoto, Y.; Sakaguchi, S.; Ito, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedron 1993, 49, 10531. (j) Fujimoto, K.; Nakai, T. Tetrahedron Lett. 1994, 35, 5019. (k) Reetz, M. T.; Griebenow, N.; Goddard, R. J. Chem. Soc. Chem. Commun. 1995, 1605. (l) Konno, T.; Umetani, H.; Kitazume, T. J. Org. Chem. 1997, 62, 137.
23. (a) Takahashi, O.; Maeda, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1355. (b) Takahashi, O.; Saka, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1599. (c) Uchikawa, M.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 4581. (d) Kuroda, S.; Katsuki, T. Yamaguchi, M. Tetrahedron Lett. 1987, 28, 803. (e) Kuroda, S.; Sakaguchi, S.; Ikegami, S.; Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1988, 29, 4763. (f) Brückner, R. Chem. Ber. 1989, 122, 703. (g) Mikami, K.; Takahashi, O.; Fujimoto, K.; Nakai, T. Synlett 1991, 629. (h) Oh, T.; Wrobel, Z.; Rubenstein, S. M. Tetrahedron Lett. 1991, 32, 4647. Marshall, J. A.; Wang, X. J. Org. Chem. 1991, 56, 4913. (i) Okamura, H.; Kuroda, S.; Ikegami, S.; Tomita, K.; Sugimoto, Y.; Sakaguchi, S.; Ito, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedron 1993, 49, 10531. (j) Fujimoto, K.; Nakai, T. Tetrahedron Lett. 1994, 35, 5019. (k) Reetz, M. T.; Griebenow, N.; Goddard, R. J. Chem. Soc. Chem. Commun. 1995, 1605. (l) Konno, T.; Umetani, H.; Kitazume, T. J. Org. Chem. 1997, 62, 137.
24. (a) Takahashi, O.; Maeda, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1355. (b) Takahashi, O.; Saka, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1599. (c) Uchikawa, M.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 4581. (d) Kuroda, S.; Katsuki, T. Yamaguchi, M. Tetrahedron Lett. 1987, 28, 803. (e) Kuroda, S.; Sakaguchi, S.; Ikegami, S.; Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1988, 29, 4763. (f) Brückner, R. Chem. Ber. 1989, 122, 703. (g) Mikami, K.; Takahashi, O.; Fujimoto, K.; Nakai, T. Synlett 1991, 629. (h) Oh, T.; Wrobel, Z.; Rubenstein, S. M. Tetrahedron Lett. 1991, 32, 4647. Marshall, J. A.; Wang, X. J. Org. Chem. 1991, 56, 4913. (i) Okamura, H.; Kuroda, S.; Ikegami, S.; Tomita, K.; Sugimoto, Y.; Sakaguchi, S.; Ito, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedron 1993, 49, 10531. (j) Fujimoto, K.; Nakai, T. Tetrahedron Lett. 1994, 35, 5019. (k) Reetz, M. T.; Griebenow, N.; Goddard, R. J. Chem. Soc. Chem. Commun. 1995, 1605. (l) Konno, T.; Umetani, H.; Kitazume, T. J. Org. Chem. 1997, 62, 137.
25. (a) Takahashi, O.; Maeda, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1355. (b) Takahashi, O.; Saka, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1599. (c) Uchikawa, M.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 4581. (d) Kuroda, S.; Katsuki, T. Yamaguchi, M. Tetrahedron Lett. 1987, 28, 803. (e) Kuroda, S.; Sakaguchi, S.; Ikegami, S.; Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1988, 29, 4763. (f) Brückner, R. Chem. Ber. 1989, 122, 703. (g) Mikami, K.; Takahashi, O.; Fujimoto, K.; Nakai, T. Synlett 1991, 629. (h) Oh, T.; Wrobel, Z.; Rubenstein, S. M. Tetrahedron Lett. 1991, 32, 4647. Marshall, J. A.; Wang, X. J. Org. Chem. 1991, 56, 4913. (i) Okamura, H.; Kuroda, S.; Ikegami, S.; Tomita, K.; Sugimoto, Y.; Sakaguchi, S.; Ito, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedron 1993, 49, 10531. (j) Fujimoto, K.; Nakai, T. Tetrahedron Lett. 1994, 35, 5019. (k) Reetz, M. T.; Griebenow, N.; Goddard, R. J. Chem. Soc. Chem. Commun. 1995, 1605. (l) Konno, T.; Umetani, H.; Kitazume, T. J. Org. Chem. 1997, 62, 137.
26. (a) Takahashi, O.; Maeda, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1355. (b) Takahashi, O.; Saka, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1599. (c) Uchikawa, M.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 4581. (d) Kuroda, S.; Katsuki, T. Yamaguchi, M. Tetrahedron Lett. 1987, 28, 803. (e) Kuroda, S.; Sakaguchi, S.; Ikegami, S.; Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1988, 29, 4763. (f) Brückner, R. Chem. Ber. 1989, 122, 703. (g) Mikami, K.; Takahashi, O.; Fujimoto, K.; Nakai, T. Synlett 1991, 629. (h) Oh, T.; Wrobel, Z.; Rubenstein, S. M. Tetrahedron Lett. 1991, 32, 4647. Marshall, J. A.; Wang, X. J. Org. Chem. 1991, 56, 4913. (i) Okamura, H.; Kuroda, S.; Ikegami, S.; Tomita, K.; Sugimoto, Y.; Sakaguchi, S.; Ito, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedron 1993, 49, 10531. (j) Fujimoto, K.; Nakai, T. Tetrahedron Lett. 1994, 35, 5019. (k) Reetz, M. T.; Griebenow, N.; Goddard, R. J. Chem. Soc. Chem. Commun. 1995, 1605. (l) Konno, T.; Umetani, H.; Kitazume, T. J. Org. Chem. 1997, 62, 137.
27. (a) Takahashi, O.; Maeda, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1355. (b) Takahashi, O.; Saka, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1599. (c) Uchikawa, M.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 4581. (d) Kuroda, S.; Katsuki, T. Yamaguchi, M. Tetrahedron Lett. 1987, 28, 803. (e) Kuroda, S.; Sakaguchi, S.; Ikegami, S.; Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1988, 29, 4763. (f) Brückner, R. Chem. Ber. 1989, 122, 703. (g) Mikami, K.; Takahashi, O.; Fujimoto, K.; Nakai, T. Synlett 1991, 629. (h) Oh, T.; Wrobel, Z.; Rubenstein, S. M. Tetrahedron Lett. 1991, 32, 4647. Marshall, J. A.; Wang, X. J. Org. Chem. 1991, 56, 4913. (i) Okamura, H.; Kuroda, S.; Ikegami, S.; Tomita, K.; Sugimoto, Y.; Sakaguchi, S.; Ito, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedron 1993, 49, 10531. (j) Fujimoto, K.; Nakai, T. Tetrahedron Lett. 1994, 35, 5019. (k) Reetz, M. T.; Griebenow, N.; Goddard, R. J. Chem. Soc. Chem. Commun. 1995, 1605. (l) Konno, T.; Umetani, H.; Kitazume, T. J. Org. Chem. 1997, 62, 137.
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32. We are aware of the lack of diastereoface differentiating ability of menthol which is well documented. Nevertheless, (-)- menthol provides a cheap commercially available mimic for the more expensive 8-phenylmenthol which can serve as a powerful chiral auxiliary and will be utilized in further studies. For a review concerning cyclohexyl-based chiral auxiliaries, see Whitesell, J. K. Chem. Rev. 1992, 92, 953.
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35. An example for the chemoselective aldol addition of a 2-allyloxy-substituted ester enolate without obtaining the possible [2,3]-Wittig rearrangement product has been reported, see Nakahara, Y.; Shimizu, M.; Yoshioka, H. Tetrahedron Lett. 1988, 29, 2325.
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41. (a) Wu, Y.-D.; Houk, K. N.; Marshall, J. A. J. Org. Chem. 1990, 55, 1421. (b) Mikami, K.; Kimura, Y.; Kishi, N; Nakai, T J. Org. Chem. 1983, 48, 281. (c) Tsai, D. J.-S.; Midland, M. M. J. Org. Chem. 1984, 49, 1842. (d) Rautenstrauch, V. J. Chem. Soc., Chem. Commun. 1970, 4.
42. Okajima, T.; Fukuzawa, Y. Chem. Lett. 1997, 81. The same effect was found to stabilize the calculated transition state of the [2,3]-Wittig rearrangement of a crotyloxy acetaldehyde enolate, see Mikami, K.; Uchida, T.; Hirano, T.; Wu, Y.; Houk, K. N. Tetrahedron 1994, 50, 5917.
43. Okajima, T.; Fukuzawa, Y. Chem. Lett. 1997, 81. The same effect was found to stabilize the calculated transition state of the [2,3]-Wittig rearrangement of a crotyloxy acetaldehyde enolate, see Mikami, K.; Uchida, T.; Hirano, T.; Wu, Y.; Houk, K. N. Tetrahedron 1994, 50, 5917.
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