Probing the "additive effect" in the proline and proline hydroxamic acid catalyzed asymmetric addition of nitroalkanes to cyclic enones

Chirality

Volumn 17, Issue 9, 2005, Pages 540-543

  Hanessian, Stephen ^a   Govindan, Subramaniyan ^a   Warrier, Jayakumar S ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

Conjugate addition; Organocatalysis; Piperazine; Proline; Proline hydroxamic acid

Indexed keywords

2 CYCLOHEXENONE; 2 NITROPROPANE; HYDROXAMIC ACID; NITROALKANE; PIPERAZINE DERIVATIVE; PROLINE;

ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; CONJUGATION; MICHAEL ADDITION; PRIORITY JOURNAL; STEREOCHEMISTRY;

ALKANES; CATALYSIS; CYCLIZATION; HYDROXAMIC ACIDS; MOLECULAR STRUCTURE; NITRO COMPOUNDS; PROLINE; STEREOISOMERISM;

EID: 27344449068     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.20201     Document Type: Article

References (41)

1. (a) Jacobson EN, Pflatz A, Yamamoto H (editors). Comprehensive asymmetric catalysis. Heidelberg, Germany: Springer; 1999.
2. (b) Ojima I. Asymmetric synthesis, 2nd edition. New York: VCH; 2000.
3. See for example: Allemann C, Gordillo R, Clemente FR, Cheong PH, Houk KN. Theory of asymmetric organocatalysis of aldol and related reactions: rationalizations and predictions. Acc Chem Res 2004;37:558-569.
4. For a general overview on synthesis planning and visual perception, see: (a) Hanessian S, Franco J, Larouche B. The psychobiological basis of heuristic synthesis planning-Man, machine, and the Chiron approach. Pure Appl Chem 1990;62:1887.
5. See also: (b) Hanessian S, Claridge S, Johnstone S. The power of visual imagery in synthesis planning. Stereocontrolled approaches to CGP-60536B, a potent renin inhibitor. J Org Chem 2002;67:4261-4274.
6. (c) Hanessian S, Parthasarathy S, Mauduit M. The power of visual imagery in drug design. Isopavines as a new class of morphinomimetics and their human opioid receptor binding activity. J Med Chem 2003;46:34-48.
7. See for example: Katsuki T, Sharpless KB. The first practical method for asymmetric epoxidation. J Am Chem Soc 1980;102:5974-5976.
8. For excellent reviews, see: (a) Dalko PI, Moisan L. In the Golden Age of organocatalysis. Angew Chem Int Ed 2004;43:5138-5175.
9. (b) Special issue on asymmetric organocatalysis. Acc Chem Res 2004;37(8).
10. (c) Dalko PI, Moisan L. Enantioselective organocatalysis. Angew Chem Int Ed 2001;40:3726-3748.
11. (d) Berkessel A, Groger H. In: Metal-free organic catalyst in asymmetric synthesis. Weinheim: Wiley-VCH; 2004.
12. (e) Banaglia M, Puglisi A, Cozzi F. Polymer-supported organic catalysts. Chem Rev 2003;103:3401-3430.
13. For early seminal examples, see: (a) Wynberg H, Staring EG. Asymmetric synthesis of (S)- and (R)-malic acid from ketene and chloral. J Am Chem Soc 1982;104:166-168.
14. (b) Staring EG, Moorlag H, Wynberg H. A highly efficient synthesis of (R)- and (S)-citramalic acid. Rec Trav Chim Pays Bas 1986;105:374.
15. For related reviews, see: (c) Kacprzak K, Gawronski J. Cinchona alkaloids and their derivatives: versatile catalysts and ligands in asymmetric synthesis. Synthesis 2001;961-999.
16. Wynberg H. Asymmetric catalysis by alkaloids. Top Stereochem 1986;16:87-129.
17. For example, see: (a) Northrup AB, Mangion IK, Hettche F, MacMillan DWC. Enantioselective organocatalytic direct aldol reactions of α-oxyaldehydes: step one in a two-step synthesis of carbohydrates. Angew Chem Int Ed 2004;43;2152-2154.
18. (b) Notz W, Tanaka F, Barbas III CF. Enamine-based organocatalysis with proline and diamines: the development of direct catalytic asymmetric aldol, Mannich, Michael, and Diels-Alder reactions. Acc Chem Res 2004;37:580-591.
19. (c) Gathergood N. Asymmetric organocatalysis: proline an essential amino acid? Aust J Chem 2002;55:615.
20. Jarvo ER, Miller SJ. Amino acids and peptides as asymmetric organocatalysts. Tetrahedron 2002;58:2481-2495.
21. (e) List B. Proline-catalyzed asymmetric reactions. Tetrahedron 2002;58:5573-5590.
22. (f) Groger H, Wilkin J. The application of L-proline as an enzyme mimic and further new asymmetric syntheses using small organic molecules as chiral catalysts. Angew Chem Int Ed 2001;40:529-532.
23. (g) List B. Asymmetric aminocatalysis. Synlett 2001;1675-1686.
24. See for example: (a) Leonard J. Control of asymmetry through conjugate addition reactions. Contemp Org Synth 1994;1:387.
25. (b) Perlmutter P. Conjugate addition reactions in organic synthesis. Oxford: Pergamon; 1992.
26. Rossiter BE, Swingle NM. Asymmetric conjugate addition. Chem Rev 1992;92:771-806.
27. For related examples of addition to chalcone and acyclic enones, see: (d) Bako D, Kiss T, Toke L. Chiral azacrown ethers derived from D-glucose as catalysts for enantioselective Michael addition. Tetrahedron Lett 1997;38:7259-7262.
28. (e) Nakajima M, Sasaki Y, Shiro M, Hashimoto S. A novel axially dissymmetric chiral ligand based on amine N-oxide: (R)- and (S)-3,3′- dimethyl-2,2′-biquinoline N,N′-dioxide. Tetrahedron Asymmetry 1997;8:341-344.
29. (f) Funabashi K, Saida Y, Kanai M, Arai T, Sasai H, Shibasaki M. Catalytic asymmetric Michael addition of nitromethane to enones controlled by (R)-LPB. Tetrahedron Lett 1998;39:7557-7558.
30. Hanessian S, Pham V. Catalytic asymmetric conjugate addition of nitroalkanes to cycloalkenones. Org Lett 2000;2:2975-2978.
31. (a) Yamaguchi M, Igarashi Y, Reddy RS, Shiraishi T, Hirama M. Asymmetric Michael addition of nitroalkanes to prochiral acceptors catalyzed by proline rubidium salts. Tetrahedron 1997;53:11223-11236.
32. For the role of additives and co-catalysts in asymmetric reactions, see: (a) Vogl EM, Groger H, Shibasaki M. Towards perfect asymmetric catalysis: additives and cocatalysts. Angew Chem Int Ed 1999;38:1570-1577.
33. (b) Rowlands GJ. Ambifunctional cooperative catalysts. Tetrahedron 2001;57:1865-1882.
34. (c) Imbriglio JE, Vasbinder MM, Miller SJ. Dual catalyst control in the amino acid-peptide-catalyzed enantioselective Baylis-Hillman reaction. Org Lett 2003;5:3741-3743.
35. Tsogoeva SB, Jagtap SB. Dual catalyst control in the chiral diamine-dipeptide-catalyzed asymmetric Michael addition. Synlett 2004;2624-2626.
36. (a) Pirrung MC, Chau JHL. A convenient procedure for the preparation of amino acid hydroxamates from esters. J Org Chem 1995;60:8084-8085.
37. 3) of the ketal with (2R,3R)-2,3-butanediol (36.60/35.54, 38.26/37.17, 44.12/43.61).
38. For an excellent review, see; Girard C, Kagan HB. Nonlinear effects in asymmetric synthesis and stereoselective reactions: ten years of investigation. Angew Chem Int Ed 1998;37:2922-2959.
39. Soai K, Hayashi H, Hasegawa H. Synthesis of (2S,5S)-2,5-bis(phenylmethyl) piperazine by the reduction with sodium borohydride using titanium tetrachloride. Heterocycles 1986;24:1287-1289.
40. Bordwell FG, Fried HE, Hughes DL, Lynch TY, Satish AV, Whang YE. Acidities of carboxamides, hydroxamic acids, carbohydrazides, benzenesulfonamides, and benzenesulfonohydrazides in DMSO solution. J Org Chem 1990;55:3330-3336.
41. For a discussion of the basicity of piperazines, see: Keyworth DA. Basicity and ionization constants of some piperazine derivatives. J Org Chem 1959;24:1355-1356.