Direct Catalytic Enantio- And Diastereoselective Aldol Reaction Using a Zn-Zn-Linked-BINOL Complex: A Practical Synthesis of syn-1,2-Diols

Organic Letters

Volumn 3, Issue 10, 2001, Pages 1539-1542

  Kumagai, Naoya ^a   Matsunaga, Shigeki ^a   Yoshikawa, Naoki ^a   Ohshima, Takashi ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

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ARTICLE;

EID: 0000148255     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015878p     Document Type: Article

References (45)

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2. (b) Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1352.
3. (c) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137.
4. (d) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. See also:
5. (e) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
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8. (c) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561.
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10. (e) Nakagawa, M.; Nakao, H.; Watanabe, K.-I. Chem. Lett. 1985.,391.
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15. For the synthesis of syn- or anti-1,2-diols by aldolases or catalytic antibodies, see: (a) Bednarski, M. D.; Simon, E. S.; Bischofberger, N.; Fessner, W.-D.; Kim, M.-J.; Lees, W.; Saito, T.; Waldmann, H.; Whitesides, G. M. J. Am. Chem. Soc. 1989, 111, 627.
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19. Notz, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386.
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21. Yoshikawa, N.; Kumagai, N.; Matsunaga, S.; Moll, G.; Ohshima, T.; Suzuki, T.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 2466.
22. For the direct catalytic asymmetric aldol reaction of acetophenones promoted by the LLB·KOH complex, the use of 3′-nitroacetophenone was effective in some cases. See ref 2b.
23. The use of hydroxyacetone gave unasatisfactory results with Zn-Zn-linked-BINOL 2. Further studies are currently under investigation.
24. No change of ee and dr was observed. For detailed procedures, see Supporting Information. Isolation of diols was also possible.
25. 3P(O) (20 mol %): -40°C, 48 h, yield 89%, synlanti = 72/28, syn = 81% ee, anti = 81% ee. See ref 9.
26. For catalytic asymmetric syntheses using linked-BINOL as ligand, see: ref 9 and the following: (a) Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252-2260.
27. (b) Kim, Y. S.; Matsunaga, S.; Das, J.; Sekine, A.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6506-6507.
28. (c) Matsunaga, S.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2000, 41, 8473-8478 and references therein.
29. 4. Evaporation of solvent gave a crude mixture of the aldol products.
30. In all cases, the reaction was quenched after an appropriate time (<24 h). A prolonged reaction time resulted in a lower ee of syn-4, probably due to the epimerization of anti-4 under the reaction conditions.
31. Review: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
32. See Supporting Information for detailed synthetic procedures.
33. Similar mechanisms are proposed for the hydrolysis of phosphates catalyzed by achiral dinuclear Zn complexes, (a) Abe, K.; Izumi, J.; Ohba, M.; Yokoyama, T.; Okawa, H. Bull. Chem. Soc. Jpn. 2001, 74, 85 and references therein. For selected examples of recent dinuclear Zn catalysts, see refs 5 and 8 and references therein. See also:
34. (b) Hikichi, S.; Tanaka, M.; Moro-oka, Y.; Kitajima, N. J. Chem. Soc., Chem. Commun. 1992, 814.
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39. (g) Bazzicalupi, C.; Bencini, A.; Bianchi, A.; Fusi, V.; Giorgi, C.; Paoletti, P.; Valtancoli, B.; Zanchi, D. Inorg. Chem. 1997, 36, 2784.
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42. (j) Kim, H.-S.; Kim, J.-J.; Lee, B.-G.; Jung, O.-S.; Jang, H.-G.; Kang, S.-O. Angew. Chem., Int. Ed. 2000, 39, 4096 and references therein.
43. The carbonate 6a was prepared by treating syn-4a with triphosgene (93% yield). See Supporting Information.
44. Tamura, Y.; Fujiwara, H.; Sumoto, K.; Ikeda, M.; Kita, Y. Synthesis 1973, 215.
45. Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 8180 and references therein.