Enantioselective allylic substitutions using ketene silyl acetals catalyzed by a palladium-chiral amidine complex

Tetrahedron Asymmetry

Volumn 9, Issue 5, 1998, Pages 741-744

  Saitoh, Akihito ^a   Achiwa, Kazuo ^a   Morimoto, Toshiaki ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDINE; KETENE DERIVATIVE; PALLADIUM;

CATALYSIS; ENANTIOMER; PRIORITY JOURNAL; REVIEW; STEREOCHEMISTRY;

EID: 0032513239     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00045-7     Document Type: Article

References (34)

1. 1. Recent review articles and books on transition metal-catalyzed organic synthesis via π-allyl complexes, see: (a) Tsuji, J. Transition Metals in Organic Synthesis Kagaku Dojin, Japan, 1997.
2. (b) Tsuji, J. Palladium Reagents and Catalysts, Innovations in Organic synthesis John Wiley, New York, 1995, p. 290.
3. (c) Godleski, S. A. Comprehensive Organic Synthesis Vol 4, Pergamon, Oxford, 1991, p. 585.
4. (d) Trost, B. M. Angew. Chem. Int. Ed. Engl. 1989, 28, 1173.
5. (e) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140.
6. (f) Heck, R. F. Palladium Reagents in Organic Synthesis Academic Press, New York, 1985. For the mechanistic understanding on palladium-catalyzed allylations, see:
7. (g) Trost, B. M.; Weber, L.; Strege, P. E.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978, 100, 3426.
8. (h) Trost, B. M.; Verhoeven, T. R. ibid. 1978, 100, 3435.
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11. (k) Hayashi, T.; Hagihara, T.; Konishi, M.; Kumada, M. ibid. 1983, 105, 7767.
12. (l) Mackenzie, P. B.; Whelan, J.; Bosnichi, B. ibid. 1985, 107, 2046.
13. 2. General reviews on palladium-catalyzed asymmetric allylic alkylations, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
14. (b) Williams, J. M. J. Synlett 1996, 705.
15. (c) Hayashi, T. In Catalytic Asymmetric Synthesis, Ed. Ojima, I., VCH, Weinheim, 1993.
16. (d) Pfalts, A. Acc. Chem. Res. 1993, 26, 339.
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18. (f) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
19. (g) Consiglio, G.; Waymouth, R. Chem. Rev. 1989, 89, 257.
20. 3. Organic synthesis using ketene silyl acetals was well compiled by Kita et al., see: Kita, Y.; Tamura, O.; Tamura, Y. J. Synth. Org. Chem. 1986, 1118.
21. 4. Saitoh, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1997, 8, 3567.
22. 3) was prepared as a 7:3 mixture with a C-silylated compound, methyl trimethylsilylacetate. Carbomethoxy ketene methyltrimethylsilyl acetal 3d tends to be hydrolyzed easily. Therefore the hydrolyzed product, dimethyl malonate was removed by distillation just before conducting the asymmetric reaction. Articles referring to the preparation of ketene silyl acetals, see: (a) Ainsworth, C.; Chen, F.; Kuo, Y.-N. J. Organomet. Chem. 1972, 46, 59.
23. (b) Rathke, M. W.; Sullivan, D. F. Synth. Commun. 1973, 3, 67.
24. (c) Kita, Y.; Haruta, J.; Segawa, J.; Tamura, Y. Tetrahedron Lett. 1979, 4311.
25. 6. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143.
26. 7. Asymmetric alkylations of cycloalkenediol derivatives using disilylamide having a ketene silyl acetal skeleton were shown in a previous paper. The silylated nucleophile was employed in order to reduce the dissociation of bisphosphine ligand from the palladium by an amide anion which was initially used as a nucleophile, see: Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016.
27. +); 293; 265; 232; 206; 193; 116.
28. 1H NMR spectrum of the residue was measured, followed by comparison of the spectrum with that of carbomethoxy ketene methyltrimethylsilyl acetal 3d. 10. Krapcho's condition is available to prepare (3S)-methyl 3,5-diphenylpent-4-enoate 5, see: (a) Krapcho, A. P.; Lovery, A. J. Tetrahedron Lett. 1973, 957.
29. (b) Krapcho, A. P.; Jahngen Jr., E.; Lovery, A. J. ibid. 1974, 1091.
30. (c) Morimoto, Y.; Shirahama, H. Tetrahedron 1996, 52, 10631.
31. 11. Among preceding articles related to palladium-catalyzed allylations without focusing on the enantioselective reaction, a study using allyl acetate and ketene silyl acetal to yield α-allylated carboxylic acid esters and cyclopropane derivatives was found. The addition of silyl enolate from the side opposite the metal was proposed, see: (a) Carfagna, C.; Mariani, L.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 3924.
32. (b) Carfagna, C.; Galarini, R.; Musco, A.; Santi, R. J. Mol. Catal. 1992, 72, 19. Tsuji et al. explored palladium-catalyzed reactions of allyl carbonates with ketene silyl acetals. It was demonstrated as a reaction mechanism that the reaction proceeded through the formation of π-allylpalladium complex by the oxidative addition of allyl carbonate, followed by decarboxylation and the addition of enolate anion to the metal, see:
33. (c) Tsuji, J.; Takahashi, K.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1984, 25, 4783. Iron complexes for the reaction of allyl acetate with ketene silyl acetal, see:
34. (d) Enders, D.; Frank, U.; Fey, P.; Jandeleit, B.; Lohray, B. B. J. Org. Chem. 1996, 579, 147.