The first organocatalysed direct aldol reaction of 2-hydroxycyclobutanone

Synlett

Volumn , Issue 5, 2011, Pages 712-716

  Aitken, David J ^a   Capitta, Francesca ^a,b   Frongia, Angelo ^a,b   Gori, Didier ^a   Guillot, Régis ^a   Ollivier, Jean ^a   Piras, Pier Paolo ^b   Secci, Francesco ^b   Spiga, Marco ^b  

^a UNIVERSITÉ PARIS SUD   (France)

^b UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

aldol reaction; cyclobutanone; organocatalysis; stereoselective reaction.; tryptophan

Indexed keywords

2 HYDROXYCYCLOBUTANONE; 2,2 DISUBSTITUTED CYCLOBUTANONE; 4 NITROBENZALDEHYDE; ALDEHYDE; BENZALDEHYDE DERIVATIVE; CYCLOBUTANONE DERIVATIVE; TRYPTOPHAN; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CRYSTAL STRUCTURE; DIRECT ALDOL REACTION; ORGANOCATALYSIS; STEREOCHEMISTRY;

EID: 79952441198     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259550     Document Type: Article

References (74)

1. Namsylo J C., Kaufmann D E., Chem. Rev. 2003 103 1485
2. Lee-Ruff E, Mladenova G, Chem. Rev. 2003 103 1449
3. Fu N.-Y, Chan S.-H, In The Chemistry of Cyclobutanes Rappoport Z Liebman J F. Wiley and Sons Chichester 2005 357
4. Lee-Ruff E, In The Chemistry of Cyclobutanes Rappoport Z Liebman J F. Wiley and Sons Chichester 2005 281
5. Bellus D, Ernst B, Angew. Chem., Int. Ed. Engl. 1988 27 797
6. Nemoto H, Fukumoto K, Synlett 1997 863
7. Salaün J, Science of Synthesis Vol. 26 Cossy J Thieme Stuttgart 2004 557
8. Miyata J, Nemoto H, Ihara M, J. Org. Chem. 2000 65 504
9. Kingsbury J S., Corey E J., J. Am. Chem. Soc. 2005 127 13813
10. Wang B, Shen Y.-M, Shi Y, J. Org. Chem. 2006 71 9519
11. Hiroi K, Nakamura H, Anzai T, J. Am. Chem. Soc. 1987 109 1250
12. Nemoto H, Nagamochi M, Fukumoto K, J. Org. Chem. 1992 57 1707
13. Nemoto H, Nagamochi M, Ishibashi H, Fukumoto K, J. Org. Chem. 1994 59 74
14. For some recent reviews on organocatalysis, see:, Melchiorre P, Marigo M, Carlone A, Bartoli G, Angew. Chem. Int. Ed. 2008 47 6138
15. Dondoni A, Massi A, Angew. Chem. Int. Ed. 2008 47 2
16. Erkkila A, Majander I, Pihko P M., Chem. Rev. 2007 107 5416
17. Mukherjee S, Yang J W., Hoffmann S, List B, Chem. Rev. 2007 107 5471
18. Pellissier H, Tetrahedron 2007 63 9267
19. Guillena G, Najera C, Ramon D J., Tetrahedron: Asymmetry 2007 18 2249
20. Dalko P I., Enantioselective Organocatalysis Wiley-VCH Weinheim 2007
21. Berkessel A, Gröger H, Asymmetric Organocatalysis Wiley-VCH Weinheim 2005
22. Zhang L, Cui L, Li X, Li J, Luo S, Cheng J.-P, Chem. Eur. J. 2010 16 2045
23. Kotrusz P, Alemayehu S, Toma S, Schmalz H.-G, Adler A, Eur. J. Org. Chem. 2005 4904
24. Kotrusz P, Kmentová I, Gotov B, Toma S, Solánioná E, Chem. Commun. 2002 2510
25. Cobb A J., Shaw D M., Longbottom D A., Gold J B., Ley S V., Org. Biomol. Chem. 2005 3 84
26. Alcaide B, Almendros P, Luna A, Tetrahedron 2007 63 3102
27. Ma X, Da C S, Yi L, Jia Y.-N, Guo Q.-P, Che L.-P, Wu F.-C, Wang J.-R, Li W.-P, Tetrahedron: Asymmetry 2009 20 1419
28. Cobb A J. A., Shaw D M., Ley S V., Synlett 2004 558
29. Alza E, Rodríguez-Escrich C, Sayalero S, Bastero A, Pericàs M A., Chem. Eur. J. 2009 15 10167
30. Veverková E, trasserová J, ebesta R, Toma, Tetrahedron: Asymmetry 2010 21 58
31. Kotrusz P, Toma S, Schmalz H.-G, Adler A, Eur. J. Org. Chem. 2004 1577
32. Alberti G, Bernard A M., Floris C, Frongia A, Piras P P., Secci F, Spiga M, Org. Biomol. Chem. 2009 7 3512
33. Frongia A, Girard C, Ollivier J, Piras P P., Secci F, Synlett 2008 2823
34. Bernard A M., Frongia A, Guillot R, Piras P P., Secci F, Spiga M, Org. Lett. 2007 9 541
35. Secci F, Frongia A, Ollivier J, Piras P P., Synthesis 2007 999
36. Bernard A M., Frongia A, Piras P P., Secci F, Org. Lett. 2003 5 2923
37. Chevtchouk T, Ollivier J, Salaün J, Tetrahedron: Asymmetry 1997 8 1011
38. Bernard A M., Frongia A, Piras P P., Secci F, Chem. Commun. 2005 3853
39. Le Liepvre M, Ollivier J, Aitken D J., Tetrahedron: Asymmetry 2010 21 1480
40. Le Liepvre M, Ollivier J, Aitken D J., Eur. J. Org. Chem. 2009 5953
41. Fernandes C, Pereira E, Faure S, Aitken D J., J. Org. Chem. 2009 74 3217
42. Mondière A, Peng R, Remuson R, Aitken D J., Tetrahedron 2008 64 1088
43. Fernandes C, Gauzy C, Yang Y, Roy O, Pereira E, Faure S, Aitken D J., Synthesis 2007 2222
44. Gauzy C, Saby B, Pereira E, Faure S, Aitken D J., Synlett 2006 1394
45. Gu X, Xian M, Roy-Faure S, Bolte J, Aitken D J., Gefflaut T, Tetrahedron Lett. 2006 47 193
46. Gauzy C, Pereira E, Faure S, Aitken D J., Tetrahedron Lett. 2004 45 7095
47. Aitken D J., Gauzy C, Pereira E, Tetrahedron Lett. 2004 45 2359
48. Aitken D J., Gauzy C, Pereira E, Tetrahedron Lett. 2002 43 6177
49. Vergne F, Partogyan K, Aitken D J., Husson H.-P, Tetrahedron 1996 52 2421
50. Bella M, Gasperi T, Synthesis 2009 1583
51. Quaternary Stereocenters: Challenge and Solutions for Organic Synthesis Christoffers J Baro A Wiley-VCH Weinheim 2005
52. Recent examples of the preparation and synthetic transformations of 2-hydroxymethyl-2-hydroxycyclobutanone derivatives:, Maulide N, Markó I E., Org. Lett. 2007 9 3757
53. Gao F, Burnell D J., J. Org. Chem. 2006 71 356
54. Zhang X, Li W Z., Synth. Commun. 2006 36 249
55. Li W Z., Zhang X, Org. Lett. 2002 4 3485
56. Kawafuchi H, Inokuchi T, Tetrahedron Lett. 2002 43 2051
57. Blanchard A N., Burnell D J., Tetrahedron Lett. 2001 42 4779
58. Hanna I, Ricard L, Tetrahedron Lett. 1999 40 863
59. Kanada R M., Taniguchi T, Ogasawara K, Chem. Commun. 1998 1755
60. Crane S N., Burnell D J., J. Org. Chem. 1998 63 5708
61. Crane S N., Jenkins T J., Burnell D J., J. Org. Chem. 1997 62 8722
62. Lin X, Kavash R W., Mariano P S., J. Org. Chem. 1996 61 7335
63. Kotsuki H, Ikishima H, Okuyama A, Heterocycles 2008 75 493; and references therein
64. Xu L.-W, Lu Y, Org. Biomol. Chem. 2008 6 2047
65. Jiang Z, Yang H, Han X, Luo J, Wong M W., Lu Y, Org. Biomol. Chem. 2010 8 1368
66. Hayashi Y, Itoh T, Nagae N, Ohkubo M, Ishikawa H, Synthesis 2008 1565
67. Ramasastry S S. V., Zhang H, Tanaka F, Barbas C F. III., J. Am. Chem. Soc. 2007 129 288
68. Ramasastry S S. V., Albertshofer K, Utsumi N, Tanaka F, Barbas C F. III., Angew. Chem. Int. Ed. 2007 46 5572
69. Utsumi N, Imai M, Tanaka F, Ramasastry S S. V., Barbas C F. III., Org. Lett. 2007 9 3445
70. Wu X, Jiang Z, Shen H.-M, Lu Y, Adv. Synth. Catal. 2007 812
71. Teo Y.-C, Tetrahedron: Asymmetry 2007 18 1155
72. Córdova A, Zou W, Dziedzic I, Ibrahem I, Reyes E, Xu Y, Chem. Eur. J. 2006 12 5383
73. Amedijkouh M, Tetrahedron: Asymmetry 2005 16 1411
74. Xu X.-Y, Wang Y.-Z, Gong L.-Z, Org. Lett. 2007 9 4247