Acylzirconocene chloride as an 'unmasked' acyl anion: Enantioselective 1,2-addition to α,β-unsaturated ketone derivatives

Angewandte Chemie - International Edition

Volumn 38, Issue 16, 1999, Pages 2395-2398

  Hanzawa, Yuji ^a   Tabuchi, Nobuhito ^a   Saito, Kosuke ^a   Noguchi, Satoshi ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Acylations; Asymmetric catalysis; P ligands; Palladium; Zirconium

Indexed keywords

KETONE DERIVATIVE; ZIRCONIUM DERIVATIVE;

ACYLATION; ARTICLE; CATALYSIS; DERIVATIZATION; DRUG SYNTHESIS; ELECTRON TRANSPORT; LIGAND BINDING; STEREOCHEMISTRY;

EID: 0033549743     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990816)38:16<2395::AID-ANIE2395>3.0.CO;2-W     Document Type: Article

References (36)

1. Y. Hanzawa, N. Tabuchi, T. Taguchi, Tetrahedron Lett. 1998, 39, 8141.
2. Reviews: a) P. Wipf, H. Jahn, Tetrahedron 1996, 52, 12853; b) J. A. Lahinger in Comprehensive Organic Synthesis, Vol. 8 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 667; c) J. Schwartz, J. A. Labinger, Angew. Chem. 1976, 88, 402; Angew. Chem. Int. Ed. Engl. 1976, 15, 333; d) C. A. Bertelo, J. Schwartz, J. Am. Chem. Soc. 1975, 97, 228.
3. Reviews: a) P. Wipf, H. Jahn, Tetrahedron 1996, 52, 12853; b) J. A. Lahinger in Comprehensive Organic Synthesis, Vol. 8 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 667; c) J. Schwartz, J. A. Labinger, Angew. Chem. 1976, 88, 402; Angew. Chem. Int. Ed. Engl. 1976, 15, 333; d) C. A. Bertelo, J. Schwartz, J. Am. Chem. Soc. 1975, 97, 228.
4. Reviews: a) P. Wipf, H. Jahn, Tetrahedron 1996, 52, 12853; b) J. A. Lahinger in Comprehensive Organic Synthesis, Vol. 8 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 667; c) J. Schwartz, J. A. Labinger, Angew. Chem. 1976, 88, 402; Angew. Chem. Int. Ed. Engl. 1976, 15, 333; d) C. A. Bertelo, J. Schwartz, J. Am. Chem. Soc. 1975, 97, 228.
5. Reviews: a) P. Wipf, H. Jahn, Tetrahedron 1996, 52, 12853; b) J. A. Lahinger in Comprehensive Organic Synthesis, Vol. 8 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 667; c) J. Schwartz, J. A. Labinger, Angew. Chem. 1976, 88, 402; Angew. Chem. Int. Ed. Engl. 1976, 15, 333; d) C. A. Bertelo, J. Schwartz, J. Am. Chem. Soc. 1975, 97, 228.
6. Reviews: a) P. Wipf, H. Jahn, Tetrahedron 1996, 52, 12853; b) J. A. Lahinger in Comprehensive Organic Synthesis, Vol. 8 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 667; c) J. Schwartz, J. A. Labinger, Angew. Chem. 1976, 88, 402; Angew. Chem. Int. Ed. Engl. 1976, 15, 333; d) C. A. Bertelo, J. Schwartz, J. Am. Chem. Soc. 1975, 97, 228.
7. a) S. Harada, T. Taguchi, N. Tabuchi, K. Narita, Y. Hanzawa, Angew. Chem. 1998, 110, 1769; Angew. Chem. Int. Ed. 1998, 37, 1696;
8. a) S. Harada, T. Taguchi, N. Tabuchi, K. Narita, Y. Hanzawa, Angew. Chem. 1998, 110, 1769; Angew. Chem. Int. Ed. 1998, 37, 1696;
9. b) Y. Hanzawa, N. Tabuchi, T. Taguchi, Tetrahedron Lett. 1998, 39, 6249. Concerning the "unmasked" acyl anion: "Acyl Anionen und deren Derivate": R. W. Saalfrank in Methoden der organischen Chemie (Houben-Weyl), 4th ed., Vol. E-19d, 1993, p. 567, and references therein.
10. b) Y. Hanzawa, N. Tabuchi, T. Taguchi, Tetrahedron Lett. 1998, 39, 6249. Concerning the "unmasked" acyl anion: "Acyl Anionen und deren Derivate": R. W. Saalfrank in Methoden der organischen Chemie (Houben-Weyl), 4th ed., Vol. E-19d, 1993, p. 567, and references therein.
11. In these palladium-catalyzed reactions, the α,β-unsaturated ketone framework was an essential factor in facilitating the reaction, since β,γ-unsaturated and saturated ketone derivatives were unreactive toward the acylzirconocene chloride under otherwise identical conditions.
12. 2 without the addition of cyclohexenone also gave 4 in 15% yield.
13. 2] also gave 2 and 3 in 14 and 41 % yields, respectively.
14. 2] also gave 2 and 3 in 14 and 41 % yields, respectively.
15. (R)-BINAP: (R)-2,2′-bis(diphenylphosphanyl)-1,1′-binaprithyl: a) H. Takaya, K. Mashima, K. Koyano, M. Yagi, H. Kumobayashi, T. Taketomi, S. Akutagawa, R. Noyori, J. Org. Chem. 1986, 51, 629; (R,R)-CHIRAPHOS: (2R,3R)-bis(diphenylphosphanyl)butane; Pd -CHIRAPHOS complex: b) Y. Yamaguchi, T. Shima, T. Yamagishi, M. Hida, Tetrahedron Lett. 1990, 31, 5049.
16. (R)-BINAP: (R)-2,2′-bis(diphenylphosphanyl)-1,1′-binaprithyl: a) H. Takaya, K. Mashima, K. Koyano, M. Yagi, H. Kumobayashi, T. Taketomi, S. Akutagawa, R. Noyori, J. Org. Chem. 1986, 51, 629; (R,R)-CHIRAPHOS: (2R,3R)-bis(diphenylphosphanyl)butane; Pd - CHIRAPHOS complex: b) Y. Yamaguchi, T. Shima, T. Yamagishi, M. Hida, Tetrahedron Lett. 1990, 31, 5049.
17. A similar observation was made by Hayashi et al. in an asymmetric reduction of allylic esters with formic acid and a Pd/chiral phosphane catalyst: T. Hayashi, H. Iwamura, M. Naito, Y. Matsumoto, Y. Uozumi, J. Am. Chem. Soc. 1994, 116, 775.
18. (R)-MOP: (R)-2-(diphenylphosphanyl)-2′-methoxy-1,1′-binaphthyl; a) T. Hayashi, J. Synth. Org. Chem. Jpn 1994, 52, 900; b) Y. Uozumi, T. Hayashi, Pure. Appl. Chem. 1992, 64, 1911; c) Y. Uozumi, N. Suzuki, A. Ogiwara, T. Hayashi, Tetrahedron 1994, 50, 4293; d) Y. Uozumi, A. Tanahashi, S.-Y. Lee, T. Hayashi, J. Org. Chem. 1993, 58, 1945.
19. (R)-MOP: (R)-2-(diphenylphosphanyl)-2′-methoxy-1,1′-binaphthyl; a) T. Hayashi, J. Synth. Org. Chem. Jpn 1994, 52, 900; b) Y. Uozumi, T. Hayashi, Pure. Appl. Chem. 1992, 64, 1911; c) Y. Uozumi, N. Suzuki, A. Ogiwara, T. Hayashi, Tetrahedron 1994, 50, 4293; d) Y. Uozumi, A. Tanahashi, S.-Y. Lee, T. Hayashi, J. Org. Chem. 1993, 58, 1945.
20. (R)-MOP: (R)-2-(diphenylphosphanyl)-2′-methoxy-1,1′-binaphthyl; a) T. Hayashi, J. Synth. Org. Chem. Jpn 1994, 52, 900; b) Y. Uozumi, T. Hayashi, Pure. Appl. Chem. 1992, 64, 1911; c) Y. Uozumi, N. Suzuki, A. Ogiwara, T. Hayashi, Tetrahedron 1994, 50, 4293; d) Y. Uozumi, A. Tanahashi, S.-Y. Lee, T. Hayashi, J. Org. Chem. 1993, 58, 1945.
21. (R)-MOP: (R)-2-(diphenylphosphanyl)-2′-methoxy-1,1′-binaphthyl; a) T. Hayashi, J. Synth. Org. Chem. Jpn 1994, 52, 900; b) Y. Uozumi, T. Hayashi, Pure. Appl. Chem. 1992, 64, 1911; c) Y. Uozumi, N. Suzuki, A. Ogiwara, T. Hayashi, Tetrahedron 1994, 50, 4293; d) Y. Uozumi, A. Tanahashi, S.-Y. Lee, T. Hayashi, J. Org. Chem. 1993, 58, 1945.
22. Optical purity was determined by HPLC on a chiralcel AD column. All isolated new compounds showed appropriate spectroscopic data (IR, NMR, MS) and correct elemental analyses or high-resolution mass spectra.
23. 3). The absolute configurations were not determined.
24. Alcohol 6 was prepared by the Shapiro reaction of cyclohexanone p-toluenesulfonylhydrazone with n-nonanal in 48% yield. R. H. Shapiro, Org. React. (N.Y.) 1976, 13, 405. See also: N. E. Schore, M. J. Knudsen J. Org. Chem. 1997, 52, 569.
25. Alcohol 6 was prepared by the Shapiro reaction of cyclohexanone p-toluenesulfonylhydrazone with n-nonanal in 48% yield. R. H. Shapiro, Org. React. (N.Y.) 1976, 13, 405. See also: N. E. Schore, M. J. Knudsen J. Org. Chem. 1997, 52, 569.
26. T. Katsuki, K. B. Sharpless, J. Am. Chem. Soc. 1980, 102, 5974.
27. V. S. Martin, S. S. Woodard, T. Katsuki, Y. Yamada, M. Ikeda, K. B. Sharpless, J. Am. Chem. Soc. 1981, 103, 6237.
28. [14] The optical purity of (R)-6 was determined by Mosher analysis.
29. Although the highly diastereoselective epoxidation of (R)-6 is possible without adding chiral tartrate, we added (-)-tartrate, whose chirality matches that of (R)-6, to improve the optical purity of epoxy alcohol 8.
30. D. P. G. Hamon, R. A. Massy-Westropp, J. L. Newton, Tetrahedron: Asymmetry 1990, 1, 771.
31. The protection of the diol 9 is required for the subsequent oxidation of the phenylselenide group; otherwise, the selenide 9 was reconverted to the epoxy alcohol 8 under the oxidation conditions.
32. Starting from epoxy alcohol 7 (49% ee), which is obtained by the first kinetic resolution of 6 with (+)-tartrate, gave (R)-2 (43% ee) on applying the same synthetic sequence. Therefore, we believe that no epimerization takes place at the quaternary alcohol carbon atom of 9 throughout the reactions.
33. a) E. J. Corey, L. S. Hegedus, J. Am. Chem. Soc. 1969, 91, 4926;
34. b) M. P. Cook, Jr., R. M. Parlman, J. Am. Chem. Soc. 1977, 99, 5225;
35. c) L. S. Hegedus, R. J. Perry, J. Org. Chem. 1985, 50, 4955;
36. d) J. Collin, J. L. Namy, F. Dallemer, H. B. Kagan, J. Org. Chem. 1991, 56, 3118.