Enantioselective organocatalytic Michael Addition of ketones to alkylidene malonates

Chirality

Volumn 24, Issue 8, 2012, Pages 600-605

  Syu, Siang En ^a   Huang, Chan Hui ^a   Chen, Ko Wei ^a   Lee, Chia Jui ^a   Das, Utpal ^a   Jang, Yeong Jiunn ^a   Lin, Wenwei ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

alkylidene malonate; ketones; Michael addition; organocatalysis; stereoselectivity

Indexed keywords

KETONE DERIVATIVE; MALONIC ACID DERIVATIVE; PYRROLIDINE DERIVATIVE; SULFIDE; SULFONE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; MICHAEL ADDITION; PRIORITY JOURNAL; STEREOCHEMISTRY;

CATALYSIS; KETONES; MALONATES; PYRROLIDINES; STEREOISOMERISM; SUBSTRATE SPECIFICITY; SULFIDES;

EID: 84864416373     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22055     Document Type: Article

References (58)

1. Marques-Lopez E, Herrera RP, Christmann M,. Asymmetric organocatalysis in total synthesis-a trial by fire. Nat Prod Rep 2010; 27: 1138-1167.
2. Grondal C, Jeanty M, Enders D,. Organocatalytic cascade reactions as a new tool in total synthesis. Nat Chem 2010; 2: 167-178.
3. Ikunaka M,. Catalytic asymmetric carbon-carbon bond formations: their evolution from biocatalysis to organocatalysis over the millennium. Org Process Res Dev 2006; 11: 495-502.
4. Nicolaou KC, Edmonds DJ, Bulger PG,. Cascade reactions in total synthesis. Angew Chem Int Ed 2006; 45: 7134-7186. (Pubitemid 44748294)
5. Dalko PI,. Enantioselective organocatalysis. Weinheim: Wiley-VCH; 2007.
6. Berkessel A, Gröger H,. Asymmetric organocatalysis. Weinheim: Wiley-VCH; 2005.
7. Dondoni A, Massi A,. Asymmetric organocatalysis: from infancy to adolescence. Angew Chem Int Ed 2008; 47: 4638-4660.
8. Hélène P,. Asymmetric organocatalysis. Tetrahedron 2007; 63: 9267-9331.
9. Perlmutter P,. Conjugate addition reactions in organic synthesis. Oxford: Pergamon; 1992.
10. Berner OM, Tedeschi L, Enders D,. Asymmetric michael additions to nitroalkenes. Eur J Org Chem 2002; 12: 1877-1894.
11. Erkkilä A, Majander I, Pihko PM,. Iminium catalysis. Chem Rev 2007; 107: 5416-5470.
12. Mukherjee S, Yang JW, Hoffmann S, List B. Asymmetric enamine catalysis. Chem Rev 2007; 107: 5471-5569.
13. Davie EAC, Mennen SM, Xu Y, Miller SJ,. Asymmetric catalysis mediated by synthetic peptides. Chem Rev 2007; 107: 5759-5812.
14. Tsogoeva SB, Recent advances in asymmetric organocatalytic 1,4-conjugate additions. Eur J Org Chem 2007; 1701-1716.
15. AlmaÅi D, Alonso DA, Nájera C,. Organocatalytic asymmetric conjugate additions. Tetrahedron: Asymmetry, 2007; 18: 299-365.
16. List B, Pojarliev P, Martin HJ,. Efficient proline-catalyzed Michael additions of unmodified ketones to nitro olefins. Org Lett 2001; 3: 2423-2425. (Pubitemid 33627142)
17. Ishii T, Fujioka S, Sekiguchi Y, Kotsuki H,. A new class of chiral pyrrolidine-pyridine conjugate base catalysts for use in asymmetric Michael addition reactions. J Am Chem Soc 2004; 126: 9558-9559. (Pubitemid 39031040)
18. Hayashi Y, Gotoh H, Hayashi T, Shoji M,. Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes. Angew Chem Int Ed 2005; 44: 4212-4215. (Pubitemid 40968498)
19. Palomo C, Vera S, Mielgo A, Gömez-Bengoa E,. highly efficient asymmetric Michael addition of aldehydes to nitroalkenes catalyzed by a simple trans-4-hydroxyprolylamide. Angew Chem Int Ed 2006; 45: 5984-5987. (Pubitemid 44408683)
20. Cao C-L, Ye M-C, Sun X-L, Tang Y,. Pyrrolidine-thiourea as a bifunctional organocatalyst: highly enantioselective Michael addition of cyclohexanone to nitroolefins. Org Lett 2006; 8: 2901-2904. (Pubitemid 44154391)
21. Mandal T, Zhao C-G,. Synthesis of prolinal dithioacetals as catalysts for the highly stereoselective Michael addition of ketones and aldehydes to β-nitrostyrenes. Tetrahedron Lett 2007; 48: 5803-5806. (Pubitemid 47068780)
22. Gu L-q, Zhao G,. 4,4'-disubstituted-L-proline catalyzes the direct asymmetric Michael addition of aldehydes to nitrostyrenes. Adv Synth Catal 2007; 349: 1629-1632.
23. Wiesner M, Revell JD, Wennemers H,. Tripeptides as efficient asymmetric catalysts for 1,4-addition reactions of aldehydes to nitroolefins-a rational approach. Angew Chem Int Ed 2008; 47: 1871-1874.
24. Wiesner M, Revell JD, Tonazzi S, Wennemers H,. Peptide catalyzed asymmetric conjugate addition reactions of aldehydes to nitroethylene-a convenient entry into γ2-amino acids. J Am Chem Soc 2008; 130: 5610-5611. (Pubitemid 351600468)
25. Tan B, Zeng X, Lu Y, Chua PJ, Zhong G,. Rational design of organocatalyst: highly stereoselective Michael addition of cyclic ketones to nitroolefins. Org Lett 2009; 11: 1927-1930.
26. Chua PJ, Tan B, Zeng X, Zhong G,. L-prolinol as a highly enantioselective catalyst for Michael addition of cyclohexanone to nitroolefins. Bioorg Med Chem Lett 2009; 19: 3915-3918.
27. Tan B, Zhu D, Zhang L, Chua PJ, Zeng X, Zhong G,. Water-more than just a green solvent: a stereoselective one-pot access to all-chiral tetrahydronaphthalenes in aqueous media. Chem Eur J 2010; 16: 3842-3848.
28. Wu C, Li W, Yang J, Liang X, Ye J,. Asymmetric organocatalytic Michael addition of anthrone to enone. Org Biomol Chem 2010; 8: 3244-3250.
29. Wang L-L, Peng L, Bai J-F, Huang Q-C, Xu X-Y, Wang L-X,. Highly organocatalytic asymmetric Michael-ketone aldol-dehydration domino reaction: straightforward approach to construct six-membered spirocyclic oxindoles. Chem Commun 2010; 46: 8064-8066.
30. Wang J, Li H, Zu L, Wang W,. Highly enantioselective organocatalytic Michael addition reactions of ketones with chalcones. Adv Synth Catal 2006; 348: 425-428. (Pubitemid 43586819)
31. Peelen TJ, Chi Y, Gellman SH,. Enantioselective organocatalytic Michael additions of aldehydes to enones with imidazolidinones: cocatalyst effects and evidence for an enamine intermediate. J Am Chem Soc 2005; 127: 11598-11599. (Pubitemid 41208736)
32. Fonseca MTH, List B,. Catalytic asymmetric intramolecular Michael reaction of aldehydes. Angew Chem Int Ed 2004; 43: 3958-3960. (Pubitemid 39257481)
33. Melchiorre P, Jørgensen KA,. Direct enantioselective Michael addition of aldehydes to vinyl ketones catalyzed by chiral amines. J Org Chem 2003; 68: 4151-4157. (Pubitemid 36622698)
34. Liu Y-Z, Zhang J, Xu P-F, Luo Y-C,. Organocatalytic asymmetric Michael addition of 1-acetylindolin-3-ones to alpha,beta-unsaturated aldehydes: synthesis of 2-substituted indolin-3-ones. J Org Chem 2011; 76: 7551-7555.
35. Borthsa CJ, Carrera DE, MacMillan DWC,. Development of a general, enantioselective organocatalytic mukaiyama-Michael reaction with alpha,beta-unsaturated aldehydes. Tetrahedron 2009; 65: 6746-6753.
36. Xie J-W, Yue L, Chen W, Du W, Zhu J, Deng J-G, Chen Y-C,. Highly enantioselective Michael addition of cyclic 1,3-dicarbonyl compounds to α,β-unsaturated ketones. Org Lett 2007; 9: 413-415.
37. Marigo M, Bertelsen S, Landa A, Jørgensen KA,. One-pot organocatalytic domino Michael-aldol and intramolecular sn2 reactions. asymmetric synthesis of highly functionalized epoxycyclohexanone derivatives. J Am Chem Soc 2006; 128: 5475-5479.
38. Hong B-C, Wu M-F, Tseng H-C, Liao J-H,. Enantioselective organocatalytic formal [3+3]-cycloaddition of α,β-unsaturated aldehydes and application to the asymmetric synthesis of (-)-isopulegol hydrate and (-)-cubebaol. Org Lett 2006; 8: 2217-2220. (Pubitemid 43998221)
39. Xiao J, Lu Y-P, Liu Y-L, Wong P-S, Loh T-P,. A new class of structurally rigid tricyclic chiral secondary amine organocatalyst: highly enantioselective organocatalytic Michael addition of aldehydes to vinyl sulfones. Org Lett 2011; 13: 876-879.
40. Murphy JJ, Quintard A, McArdle P, Alexakis A, Stephens JC,. Asymmetric organocatalytic 1,6-conjugate addition of aldehydes to dienic sulfones. Angew Chem Int Ed 2011; 50: 5095-5098.
41. Landa A, Maestro M, Masdeu C, Puente Á, Vera S, Oiarbide M, Palomo C,. Highly enantioselective conjugate additions of aldehydes to vinyl sulfones. Chem Eur J 2009; 15: 1562-1565.
42. Sulzer-Mossé S, Alexakis A, Mareda J, Bollot G, Bernardinelli G, Filinchuk Y,. Enantioselective organocatalytic conjugate addition of aldehydes to vinyl sulfones and vinyl phosphonates as challenging Michael acceptors. Chem Eur J 2009; 15: 3204-3220.
43. Zhu Q, Lu Y,. Organocatalytic Michael addition of aldehydes to vinyl sulfones: enantioselective α-alkylations of aldehydes and their derivatives. Org Lett 2008; 10: 4803-4806.
44. Zhu Q, Cheng L, Lu Y,. Asymmetric organocatalytic Michael addition of ketones to vinyl sulfone. Chem Commun 2008; 47: 6315-6317.
45. Mossé S, Alexakis A,. First organocatalyzed asymmetric Michael addition of aldehydes to vinyl sulfones. Org Lett 2005; 7: 4361-4364. (Pubitemid 41436647)
46. Lu J, Zhou W-J, Liu F, Loha T-P,. Organocatalytic and enantioselective direct vinylogous Michael addition to maleimides. Adv Synth Catal 2008; 350: 1796-1800.
47. Zhao G-L, Xu Y, Sunden H, Eriksson L, Sayah M, Cordova A,. Organocatalytic enantioselective conjugate addition of aldehydes to maleimides. Chem Commun 2007; 734-735. (Pubitemid 46233546)
48. Sulzer-Mossé S, Tissot M, Alexakis A,. First enantioselective organocatalytic conjugate addition of aldehydes to vinyl phosphonates. Org Lett 2007; 9: 3749-3752.
49. Magar DR, Chang C, Ting Y-F, Chen K,. Highly enantioselective conjugate addition of ketones to alkylidene malonates catalyzed by a pyrrolidinyl-camphor- derived organocatalyst. Eur J Org Chem 2010; 2010: 2062-2066.
50. Liu J, Yang Z, Liu X, Wang Z, Liu Y, Bai S, Lin L, Feng X,. Organocatalyzed highly stereoselective Michael addition of ketones to alkylidene malonates and nitroolefins using chiral primary-secondary diamine catalysts based on bispidine. Org Biomol Chem 2009; 7: 4120-4127.
51. Chowdhury R, Ghosh SK,. Highly regio- and enantioselective organocatalytic conjugate addition of alkyl methyl ketones to a β-silylmethylene malonate. Org Lett 2009; 11: 3270-3273.
52. Cao C-L, Sun X-L, Zhou J-L, Tang Y,. Enantioselectively organocatalytic Michael addition of ketones to alkylidene malonates. J Org Chem 2007; 72: 4073-4076. (Pubitemid 46846949)
53. Zhao G-L, Vesely J, Sun J, Christensen KE, Bonneau C, Cõrdova A,. Organocatalytic highly enantioselective conjugate addition of aldehydes to alkylidene malonates. Adv Synth Catal 2008; 350: 657-661.
54. Betancort JM, Sakthivel K, Thayumanavan R, Barbas, III CF,. Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates. Tetrahedron Lett 2001; 42: 4441-4444. (Pubitemid 32544571)
55. S S-e, Kao T-T, Lin W,. A new type of organocatalyst for highly stereoselective Michael addition of ketones to nitroolefins on water. Tetrahedron 2010; 66: 891-897.
56. Liu P-M, Chang C, Reddy RJ, Ting Y-F, Kuan H-H, Chen K,. Remarkable reaction rate and excellent enantioselective direct α-amination of aldehydes with azodicarboxylates catalyzed by pyrrolidinylcamphor-derived organocatalysts. Eur J Org Chem 2010; 42-46.
57. Rappoport Z, Gazit A,. Effect of halogen and of a para substituent on the solid-state conformation of several crowded electrophilic vinyl halides. J Org Chem 1986; 51: 4107-4111.
58. Betancort JM, Sakthivel K, Thayumanavan R, Tanaka F, Barbas CF,. Catalytic direct asymmetric Michael reactions: addition of unmodified ketone and aldehyde donors to alkylidene malonates and nitro olefins. Synthesis 2004; 1509-1521. (Pubitemid 38898673)