Novel chiral bisformamide-promoted asymmetric allylation of benzaldehyde with allyltrichlorosilane

Synthetic Communications

Volumn 41, Issue 24, 2011, Pages 3627-3634

  Ishimaru, Kaori ^a   Ono, Kaori ^a   Tanimura, Yuya ^a   Kojima, Takakazu ^a  

^a NATIONAL DEFENSE ACADEMY   (Japan)

Author keywords

Aldehyde; Allylation; Bisformamide; Lewis base

Indexed keywords

1,2 DIAMINOCYCLOHEXANE; ALLYLTRICHLOROSILANE; BENZALDEHYDE; BISFORMAMIDE; FORMAMIDE DERIVATIVE; LEWIS BASE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER;

EID: 80052041966     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.519841     Document Type: Article

References (33)

1. (a) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; J. Otera (Ed.); Wiley-VCH: Weinheim, 2000; Chap. 10, pp. 299-402;
2. (b) Yamamoto, H. (Ed.). In Lewis Acids in Organic Synthesis; Wiley-VCH: Weinheim, 2001; Vols. 1 and 2;
3. (c) Denmark, S. E.; Fu, J. Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones. Chem. Rev. 2003, 103, 2763-2793.
4. For reviews, see (a) Kennedy, J. W. J.; Hall, D. G. Recent advances in the activation of boron and silicon reagents for stereocontrolled allylation reactions. Angew. Chem. Int. Ed. 2003, 42, 4732-4739; (Pubitemid 37314598)
5. (b) Rendler, S.; Oestreich, M. Hypervalent silicon as a reactive site in selective bond-forming processes. Synthesis 2005, 1727-1747; (Pubitemid 41058552)
6. (c) Orito, Y.; Nakajima, M. Lewis base-catalyzed asymmetric reactions involving hypervalent silicate intermediates. Synthesis 2006, 1391-1401; see also Ref. 1c. (Pubitemid 43724680)
7. For a recent review of organocatalysts, see Dalko, P. I.; Moisan, L. In the golden age of organocatalysis. Angew. Chem. Int. Ed. 2004, 43, 5138-5175. (Pubitemid 39382534)
8. 0-bipyridine-type N-monoxides as organocatalysts in the enantio-selective allylation of aldehydes with allyltrichlorosilane. Org. Lett. 2002, 4, 1047-1049;
9. (b) Malkov, A. V.; Dufkova, L.; Farrugia, L.; Kocovsky, P. Quinox, a quinoline-type N-oxide, as organocatalyst in the asymmetric allylation of aromatic aldehydes with allyl-trichlorosilanes: The role of arene-arene interactions. Angew. Chem. Int. Ed. 2003, 42, 3674-3677; (Pubitemid 37010656)
10. (c) Malkov, A. V.; Mark, B.; Orsini, M.; Pernazza, D.; Massa, A.; Herrmann, P.; Meghani, P.; Kocovsky, P. New Lewis-basic N-oxides as chiral organocatalysts in asymmetric allylation of aldehydes. J. Org. Chem. 2003, 68, 9659-9668; (Pubitemid 37509873)
11. (d) Malkov, A. V.; Bell, M.; Vassieu, M.; Bugatti, V.; Kocovsky, P. New pyridine-derived N-oxides as chiral organocatalysts in asymmetric allylation of aldehydes. J. Mol. Catal. A 2003, 196, 179-186;
12. (e) Traverse, J. F.; Zhao, Y.; Hoveyda, A. H.; Snapper, M. L. Proline-based N-oxides as readily available and modular chiral catalysts: Enantioselective reactions of allyltrichlorosilane with aldehydes. Org. Lett. 2005, 7, 3151-3154; (Pubitemid 41059094)
13. (f) Simonini, V.; Benaglia, M.; Pignataro, L.; Guizzetti, S.; Celentano, G. A new class of chiral Lewis basic metal-free catalysts for stereoselective allylations of aldehydes. Synlett 2008, 1061-1065. (Pubitemid 351613093)
14. 0-dioxide as an efficient catalyst for enantioselective addition of allyltrichlorosilanes to aldehydes. J. Am. Chem. Soc. 1998, 120, 6419-6420; (Pubitemid 28346425)
15. 0-bipyridine N,N-dioxide: Its preparation and use for asymmetric allylation of aldehydes with allyl(trichloro)silane as a highly efficient catalyst. Org. Lett. 2002, 4, 2799-2801;
16. 0-dioxides. Synlett. 2008, 3141-3144; see also Ref. 4c.
17. 00-terpyridine tri-N-oxide ligands for Lewis base-catalyzed asymmetric allylation of aldehydes. Org. Biomol. Chem. 2004, 2, 1967-1969.
18. (a) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. Asymmetric allylation of aldehydes with chiral Lewis bases. J. Org. Chem. 1994, 59, 6161-6163;
19. (b) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Asymmetric allylation of aldehydes catalyzed by substoichiometric amounts of chiral phosphoramides. Tetrahedron Lett. 1996, 37, 5149-5150; (Pubitemid 26315285)
20. (c) Bennani, Y.; Hanessian, S. The asymmetric synthesis of a-substituted a-methyl and a-phenyl phosphonic acids: Design, carbanion geometry, reactivity, and preparative aspects of chiral alkyl bicyclic phosphonamides. Tetrahedron 1996, 52, 13837-13866; (Pubitemid 26356409)
21. (d) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Asymmetric allylation of aromatic aldehydes catalyzed by chiral phosphoramides prepared from (S)-proline. Tetrahedron 1997, 53, 3513-3526; (Pubitemid 27110854)
22. (e) Denmark, S. E.; Su, X.; Nishigaichi, Y.; Coe, D. M.; Wong, K.-T.; Winter, S. B. D.; Choi, J. Y. Synthesis of phosphoramides for the Lewis base-catalyzed allylation and aldol addition reactions. J. Org. Chem. 1999, 64, 1958-1967; (Pubitemid 29152744)
23. (f) Denmark, S. E.; Fu, J.; Coe, D. M.; Su, X.; Pratt, N. E.; Griedel, B. D. Chiral phosphoramide-catalyzed enantioselective addition of allylic trichlorosilanes to aldehydes: Preparative and mechanistic studies with monodentate phosphorus-based amides. J. Org. Chem. 2006, 71, 1513-1522;
24. (g) Nemoto, T.; Hitomi, T.; Nakamura, H.; Jin, L.; Hatano, K.; Hamada, Y. Synthesis of novel P-stereogenic phenylphosphona-mides and their application to Lewis base-catalyzed asymmetric allylation of benzal-dehyde. Tetrahedron: Asymmetry 2007, 18, 1844-1849. (Pubitemid 47362636)
25. 0-bispyrrolidine-based bisphosphoramide. J. Am. Chem. Soc. 2001, 123, 9488-9489. (Pubitemid 32900337)
26. Kotani, S.; Hashimoto, S.; Nakajima, M. Chiral phosphine oxide BINAPO as a Lewis base catalyst for asymmetric allylation and aldol reaction of trichlorosilyl compounds. Tetrahedron 2007, 63, 3122-3132. (Pubitemid 46365776)
27. (a) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. A chiral formamide: Design and application to catalytic asymmetric synthesis. Tetrahedron Lett. 1998, 39, 2767-2770; (Pubitemid 28186673)
28. (b) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Asymmetric allylation with chiral formamide catalysts. Tetrahedron 1999, 55, 977-988. (Pubitemid 29045612)
29. Angell, R. M.; Barrett, A. G. M.; Braddock, D. C.; Swallow, S.; Vickery, B. D. Enantio-selective synthesis of homoallylic alcohols using (E)-but-2-enyl-trichlorosilane and chiral diamines. Chem. Commun. 1997, 919-920. (Pubitemid 127696164)
30. Liu, L.; Sun, J.; Liu, N.; Chang, W.; Li, J. A structurally simple L-proline derivative promotes the asymmetric allylation of aldehydes with tribromoallyltin. Tetrahedron: Asymmetry 2007, 18, 710-716. (Pubitemid 46590720)
31. Wen, Y.; Xiong, Y.; Chang, L.; Huang, J.; Liu, X.; Feng, X. Chiral bisformamides as effective organocatalysts for the asymmetric one-pot, three-component Strecker reaction. J. Org. Chem. 2007, 72, 7715-7719. (Pubitemid 47501640)
32. Ishimaru, K.; Monda, K.; Yamamoto, Y.; Akiba, K.-Y. Novel cationic titanium(IV) Lewis acids and their use in asymmetric aldol reactions. Tetrahedron 1998, 54, 727-734, and the references therein (Pubitemid 28035612)
33. Absolute configuration of the major enantiomer was assigned by comparing the retention time. See Pignataro, L.; Benaglia, M.; Annunziata, R.; Cinquini, M.; Cozzi, F. Structurally simple pyridine N-oxides as efficient organocatalysts for the enantioselective allylation of aromatic aldehydes. J. Org. Chem. 2006, 71, 1458-1463.