Modular amino acids-based chiral ligands for copper-catalyzed enantioselective conjugation addition of diethylzinc to cyclic enones

Chirality

Volumn 23, Issue 2, 2011, Pages 105-112

  Gou, Shaohua ^a   Judeh, Zaher M A ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

alkylation; amino acids; conjugate addition; diethylzinc; enones

Indexed keywords

3 ETHYL 4,4 DIMETHYLCYCLOHEXANONE; 3 ETHYL CYCLOHEPTANONE; 3 ETHYLCYCLOHEXANONE; AMINO ACID; COPPER; CYCLIC ENONE DERIVATIVE; DIETHYLZINC; KETONE DERIVATIVE; LIGAND; N (4 TOLUENESULFONYL) PHENYLALANINE 1 (4 METHOXYPHENYL) ETHYLAMIDE; N (4 TOLUENESULFONYL) PHENYLALANINE 2 ISOPROPYLPHENYLAMIDE; N (4 TOLUENESULFONYL) PHENYLALANINE 2 METHOXY 5 METHYLPHENYLAMIDE; N (4 TOLUENESULFONYL) PHENYLALANINE 2 METHOXYBENZYLAMIDE; N (4 TOLUENESULFONYL) PHENYLALANINE 2 METHOXYPHENYLAMIDE; N (4 TOLUENESULFONYL) PHENYLALANINE 2 PHENOXYLPHENYLAMIDE; N (4 TOLUENESULFONYL) PHENYLALANINE 3 METHOXYBENZYLAMIDE; N (4 TOLUENESULFONYL) PHENYLALANINE 3 METHOXYPHENYLAMIDE; N (4 TOLUENESULFONYL) PHENYLALANINE 4 METHOXYBENZYLAMIDE; N (4 TOLUENESULFONYL) PHENYLALANINE 4 METHOXYPHENYLAMIDE; N (4 TOLUENESULFONYL) PHENYLALANINE BENZYLAMIDE; N (4 TOLUENESULFONYL) PHENYLALANINE O TOLYLAMIDE; N (4 TOLUENESULFONYL) PHENYLALANINE PHENYLAMIDE; UNCLASSIFIED DRUG;

ADDITION LINE; ARTICLE; CATALYSIS; CHIRALITY; CONJUGATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SYNTHESIS;

CATALYSIS; COPPER; KETONES; LIGANDS; ORGANOMETALLIC COMPOUNDS; PHENYLALANINE; STEREOISOMERISM;

EID: 78650935762     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20881     Document Type: Article

References (61)

1. Tomioka K,. Conjugate addition of organometallic reagents. In:, Jacobsen EN, Pfaltz A, Yamamoto H, editor. Comprehensive asymmetric catalysis. Verlag, Berlin, Heidelberg, NY: Springer; 2004. Volume Supplement to Chapter 31.1.
2. Tomioka K, Nagaoka Y,. Conjugate addition of organometallic reagents. In:, Jacobsen EN, Pfaltz A, Yamamoto H, editors. Comprehensive asymmetric catalysis, Vol. 3. New York: Springer-Verlag; 1999. p 1105-1120.
3. Feringa BL, de Vries AHM,. Carbon-carbon bond formation by catalytic enantioselective conjugate addition. In:, Doyle M, editor. Advances in catalytic processes, Vol. 1. Greenwich, CT: JAI Press; 1995. p 151-192.
4. Alexakis A, Bäckvall JE, Krause N, Pàmies O, Diéguez M,. Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions. Chem Rev 2008; 108: 2796-2823.
5. Harutyunyan SR, den Hartog T, Geurts K, Minnaard AJ, Feringa BL,. Catalytic asymmetric conjugate addition and allylic alkylation with Grignard reagents. Chem Rev 2008; 108: 2824-2852.
6. Krause N, Hoffmann-Röder A,. Recent advances in catalytic enantioselective Michael additions. Synthesis 2001; 2: 171-196.
7. Alexakis A, Benhaim C,. Enantioselective copper-catalysed conjugate addition. Eur J Org Chem 2002; 2002: 3221-3236.
8. Feringa BL,. Phosphoramidites: marvellous ligands in catalytic asymmetric conjugate addition. Acc Chem Res 2000; 33: 346-353.
9. Sibi MP, Manyem S,. Enantioselective conjugate additions. Tetrahedron 2000; 56: 8033-8061.
10. Alexakis A, Vastra J, Burton J, Mangeney P,. Asymmetric conjugate addition of diethyl zinc to enones with tartrate chiral phosphite ligands. Tetrahedron: Asymmetry 1997; 8: 3193-3196. (Pubitemid 27451859)
11. 2 or trivalent phosphorus ligands. Tetrahedron Lett 1997; 38: 7745-7748. (Pubitemid 27463513)
12. Alexakis A, Vastra J, Burton J, Benhaim C, Mangeney P,. Asymmetric conjugate addition of diethyl zinc to enones with chiral phosphorus ligands derived from TADDOL. Tetrahedron Lett 1998; 39: 7869-7872.
13. Pàmies O, Net G, Ruiz A, Claver C,. Enantioselective copper-catalysed 1,4-addition of diethylzinc to cyclohexenone using chiral diphosphite ligands. Tetrahedron: Asymmetry 1999; 10: 2007-2014.
14. Alexakis A, Burton J, Vastra J, Benhaim C, Fournioux X, van den Heuvel A, Leveque JM, Maze F,. Synthesis and application of chiral phosphorus ligands derived from TADDOL for the asymmetric conjugate addition of diethyl zinc to enones. Eur J Org Chem 2000; 2000: 4011-4027.
15. Escher IH, Pfaltz A,. New chiral oxazoline-phosphite ligands for the enantioselective copper-catalyzed 1,4-addition of organozinc reagents to enones. Tetrahedron 2000; 56: 2879-2888.
16. Liang, Au-Yeung TTL, Chan ASC,. Highly enantioselective 1,4-addition of diorganozinc reagents to cyclic enones using chiral diphosphite ligands derived from H8-binaphthol. Org Lett 2002; 4: 3799-3801.
17. Cramer N, Laschat S, Baro A,. Chiral phosphites and phosphoramidites based on the tropane skeleton and their application in catalysis. Organometallics 2006; 25: 2284-2291.
18. Kawamura K, Fukuzawa H, Hayashi M,. Novel N,N,P-tridentate ligands for the highly enantioselective copper-catalyzed 1,4-addition of dialkylzincs to enones. Org Lett 2008; 10: 3509-3512.
19. Yan M, Yang LW, Wong KY, Chan ASC,. Enantioselective conjugate addition of diethylzinc to enones catalyzed by a copper complex of chiral aryl diphosphite. Chem Commun 1999: 11-12. (Pubitemid 29037528)
20. Yan M, Chan ASC,. Enantioselective conjugate addition of diethylzinc to cyclic enones with chiral aryl diphosphite-copper catalysts. Tetrahedron Lett 1999; 40: 6645-6648. (Pubitemid 29400632)
21. Feringa B, Pineschi M, Arnold LA, Imbos R, de Vries AHM,. Highly enantioselective catalytic conjugate addition and tandem conjugate addition-aldol reactions of organozinc reagents. Angew Chem Int Ed Engl 1997; 36: 2620-2623.
22. Naasz R, Arnold LA, Pineschi M, Keller E, Feringa BL,. Catalytic enantioselective annulations via 1,4-addition-aldol cyclization of functionalized organozinc reagents. J Am Chem Soc 1999; 121: 1104-1105.
23. Arnold LA, Imbos R, Mandoli A, de Vries AHM, Naasz R, Feringa BL,. Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; ligand variation and non-linear effects. Tetrahedron 2000; 56: 2865-2878.
24. Zhou H, Wang W-H, Fu Y, Xie J-H, Shi W-J, Wang L-X, Zhou Q-L,. Highly enantioselective copper-catalyzed conjugate addition of diethylzinc to enones using chiral spiro phosphoramidites as ligands. J Org Chem 2003; 68: 1582-1584.
25. Alexakis A, Polet D, Rosset S, March S,. Biphenol-based phosphoramidite ligands for the enantioselective copper-catalyzed conjugate addition of diethylzinc. J Org Chem 2004; 69: 5660-5667.
26. Boeda F, Rix D, Clavier H, Crévisy C, Mauduit M,. Design and synthesis of new bidentate phosphoramidite ligands for enantioselective copper-catalyzed conjugate addition of diethylzinc to enones. Tetrahedron: Asymmetry 2006; 17: 2726-2729.
27. Fuchs N, d'Augustin M, Humam M, Alexakis A, Taras R, Gladiali S,. Asymmetric conjugate addition of metal alkyl reagents catalyzed by copper complexes with BINPO: a hemilabile P,O-heterobidentate axially chiral ligand. Tetrahedron: Asymmetry 2005; 16: 3143-3146.
28. Knöbel AKH, Escher IH, Pfaltz A,. Enantioselective copper-catalyzed 1,4-addition of organozinc reagents to enones using chiral oxazoline-phosphite ligands. Synlett 1997; 12: 1429-1431.
29. Hu X, Chen HL, Zhang XM,. Development of new chiral P,N ligands and their application in the Cu-catalyzed enantioselective conjugate addition of diethylzinc to enones. Angew Chem Int Ed 1999; 38: 3518-3521.
30. Helmchen G, Pfaltz A,. Phosphinooxazolines: a new class of versatile, modular P,N-ligands for asymmetric catalysis. Acc Chem Res 2000; 33: 336-345.
31. Mizutani H, Degrado SJ, Hoveyda AH,. Cu-catalyzed asymmetric conjugate additions of alkylzinc reagents to acyclic aliphatic enones. J Am Chem Soc 2002; 124: 779-781. (Pubitemid 34112787)
32. Chataigner I, Gennari C, Ongeri S, Piarulli U, Ceccarelli S,. Discovery of a new efficient chiral ligand for copper-catalyzed enantioselective Michael additions by high-throughput screening of a parallel library13. Chem-Eur J 2001; 7: 2628-2634.
33. 2Zn to nitroolefins by high-throughput screening of a parallel library. Eur J Org Chem 2001; 4: 803-807.
34. Chataigner I, Gennari C, Piarulli U, Ceccarelli S,. Discovery of a new efficient chiral ligand for copper-catalyzed enantioselective Michael additions by high-throughput screening of a parallel library13. Angew Chem Int Ed Engl 2000; 39: 916-918.
35. Wendisch V, Sewald N,. Enantioselective copper(I) catalyzed 1,4-addition of diethylzinc to cyclohexenone: asymmetric induction as an unexpected source of structural information. Tetrahedron: Asymmetry 1997; 8: 1253-1257.
36. Nakagawa Y, Matsumoto K, Tomioka K,. Approach to enantioselective conjugate addition of organocopper reagents to cycloalkenones by the aid of chiral lactam bearing phosphine group. Tetrahedron 2000; 56: 2857-2863.
37. Guillen F, Winn CL, Alexakis A,. Enantioselective copper-catalyzed conjugate addition using chiral diaminocarbene ligands. Tetrahedron: Asymmetry 2001; 12: 2083-2086.
38. 2. Tetrahedron: Asymmetry 2001; 12: 2087-2089.
39. Clavier H, Coutable L, Toupet L, Guillemin J-C, Mauduit M,. Design and synthesis of new bidentate alkoxy-NHC ligands for enantioselective copper-catalyzed conjugate addition. J Organomet Chem 2005; 690: 5237-5254. (Pubitemid 41564133)
40. Clavier H, Coutable L, Guillemin J-C, Mauduit M,. New bidentate alkoxy-NHC ligands for enantioselective copper-catalysed conjugate addition. Tetrahedron: Asymmetry 2005; 16: 921-924.
41. Winn CL, Guillen F, Pytkowicz J, Roland S, Mangeney P, Alexakis A,. Enantioselective copper catalysed 1,4-conjugate addition reactions using chiral N-heterocyclic carbenes. J Organomet Chem 2005; 690: 5672-5695.
42. 2 to carbonyl compounds. Org Lett 2001; 3: 4259-4262.
43. Borner C, Dennis MR, Sinn E, Woodward S,. Copper-catalysed asymmetric 1,4-addition of organozinc compounds to linear aliphatic enones using 2,2′-dihydroxy 3,3′-dithioether derivatives of 1,1′- binaphthalene. Eur J Org Chem 2001; 13: 2435-2446.
44. Bennett SMW, Brown SM, Cunningham A, Dennis MR, Muxworthy JP, Oakley MA, Woodward S,. Copper-catalysed asymmetric conjugate addition of organometallic reagents to linear enones. Tetrahedron 2000; 56: 2847-2855.
45. Pàmies O, Net G, Ruiz A, Claver C, Woodward S,. Copper-catalysed asymmetric conjugate addition of organometallic reagents to enones using S,O-ligands with a xylofuranose backbone. Tetrahedron: Asymmetry 2000; 11: 871-877.
46. Bennett S, Brown SM, Conole G, Dennis MR, Fraser PK, Radojevic S, McPartlin M, Topping CM, Woodward S,. Catalytic conjugate addition promoted by the copper(I)-monothiobinaphthol system, Part 3: Comparison of three thiolate-based catalytic systems. J Chem Soc Perkin Trans 1 1999; 21: 3127-3132.
47. Kang J, Lee JH, Lim DS,. Stereoselective conjugate addition of diethylzinc to enones and nitroalkenes. Tetrahedron: Asymmetry 2003; 14: 305-315.
48. Arink AM, Braam TW, Keeris R, Jastrzebski JTBH, Benhaim C, Rosset S, Alexakis A, van Koten G,. Copper(I) thiolate catalysts in asymmetric conjugate addition reactions. Org Lett 2004; 6: 1959-1962.
49. Shi M, Wang CJ, Zhang W,. Enantioselective conjugate addition of dialkylzinc and diphenylzinc to enones catalyzed by a chiral copper(I) binaphthylthiophosphoramide or binaphthylselenophosphoramide ligand system. Chem-Eur J 2004; 10: 5507-5516.
50. Shi M, Zhang W,. Asymmetric 1,4-addition of diethylzinc to cyclic enones catalyzed by Cu(I)-chiral sulfonamide-thiophosphoramide ligands and lithium salts. Adv Synth Catal 2005; 347: 535-540.
51. Richmond ML, Seto CT,. Modular ligands derived from amino acids for the enantioselective addition of organozinc reagents to aldehydes. J Org Chem 2003; 68: 7505-7508.
52. Wu J, Mampreian DM, Hoveyda AH,. Enantioselective synthesis of nitroalkanes bearing all-carbon quaternary stereogenic centers through Cu-catalyzed asymmetric conjugate additions. J Am Chem Soc 2005; 127: 4584-4585.
53. Luchaco-Cullis CA, Hoveyda AH,. Cu-catalyzed enantioselective conjugate addition of alkylzincs to cyclic nitroalkenes: catalytic asymmetric synthesis of cyclic (±)-substituted ketones. J Am Chem Soc 2002; 124: 8192-8193.
54. Castro L, Tlahuext M, Antonio R, Benavides T, Tlahuext H,. Synthesis and structural studies of new N-(p-toluenesulfonyl)amino acid o-phenolamides. Heteroatom Chem 2003; 14: 247-253.
55. Grotjahn DB, Groy TL,. Formation of coordinatively unsaturated Cp*Ir-amino acid complexes and their highly diastereoselective complexation reactions. J Am Chem Soc 2002; 116: 6969-6970.
56. Degrado SJ, Mizutani H, Hoveyda AH,. Modular peptide-based phosphine ligands in asymmetric catalysis: efficient and enantioselective Cu-catalyzed conjugate additions to five-, six-, and seven-membered cyclic enones. J Am Chem Soc 2001; 123: 755-756.
57. Alexakis A, Benhaim C, Rosset S, Humam M,. Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions. J Am Chem Soc 2002; 124: 5262-5263.
58. Brubaker GR, Brown JN, Yoo MK, Kutchan TM, Mottel EA,. Crystal and molecular structures of (1,8-bis(2-pyridyl)-3,6-dithiaoctane)copper(I) hexafluorophosphate and perchlorato(1,8-bis(2-pyridyl)-3,6-dithiaoctane) copper(II) perchlorate: stereodynamics of the copper(II)-copper(I) couple. Inorg Chem 1979; 18: 299-302.
59. Yamamoto H, editor. Lewis acid in organic synthesis. Weinheim: Wiley-VCH, 2000.
60. Kitamura M, Miki T, Nakano K, Noyori R,. 1,4-Addition of diorganozincs to α,β-unsaturated ketones catalyzed by a copper(I)-sulfonamide combined system. Bull Chem Soc Jpn 2000: 73: 999-1014.
61. Nakano K, Bessho Y, Kitamura M,. 1,4-Addition of diethylzinc to cyclohexenone catalyzed by CuOTf-sulfonamide combined system. Evidence supporting a concerted mechanism. Chem Lett 2003; 32: 224-225.