Chiral linker 5: scope and limitations of arylsubstituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for diastereoselective syntheses

Tetrahedron Asymmetry

Volumn 20, Issue 3, 2009, Pages 273-287

  Broeker, Joachim ^a   Knollmueller, Max ^a   Gaertner, Peter ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXY 2 PHENYLHEXANOIC ACID 1,2 BIS(2 METHOXYPHENYL) 2 (2 METHYLPROPOXY)ETHYL ESTER; 2 HYDROXY 2 PHENYLHEXANOIC ACID 2 (2 METHOXYETHOXY) 1,2 BIS(2 METHOXYPHENYL)ETHYL ESTER; 2 METHYL 3 (4 NITROPHENYL)PROPANOIC ACID 1,2 BIS(2 METHOXYPHENYL) 2 (2 METHYLPROPOXY)ETHYL ESTER; 2 METHYL 3 (4 NITROPHENYL)PROPANOIC ACID 1,2 BIS(2 METHYLPHENYL) 2 (2 METHYLPROPOXY)ETHYL ESTER; 2 METHYL 3 PHENYLPROPANOIC ACID 1,2 BIS(2 METHOXYPHENYL) 2 (2 METHYLPROPOXY)ETHYL ESTER; 2 METHYL 3 PHENYLPROPANOIC ACID 1,2 BIS(2 METHYLPHENYL) 2 (2 METHYLPROPOXY)ETHYL ESTER; 2 METHYL 3 PHENYLPROPANOIC ACID 1,2 BIS(4 METHOXYPHENYL) 2 (2 METHYLPROPOXY)ETHYL ESTER; 2 METHYL 3 PHENYLPROPANOIC ACID 2 (2 METHOXYETHOXY) 1,2 BIS(2 METHOXYPHENYL)ETHYL ESTER; 2 METHYL 3 PHENYLPROPANOIC ACID 2 (2 METHYLPROPOXY) 1,2 BIS[2 (TRIFLUOROMETHYL)PHENYL]ETHYL ESTER; 3 METHYL 2 (2 METHYL 3 PHENYL PROPIONYLAMINO)BUTYRIC ACID METHYL ESTER; ACRYLIC ACID; BICYCLO[2.2.1]HEPT 5 EN 2 CARBOXYLIC ACID 1,2 BIS(2 METHOXYPHENYL) 2 (2 METHYLPROPOXY)ETHYL ESTER; BICYCLO[2.2.1]HEPT 5 EN 2 CARBOXYLIC ACID 2 (2 METHOXYETHOXY) 1,2 BIS(2 METHOXYLPHENYL)ETHYL ESTER; BICYCLO[2.2.1]HEPT 5 EN 2 CARBOXYLIC ACID 2 (2 METHOXYETHOXY) 1,2 DIPHENYLETHYL ESTER; BICYCLO[2.2.1]HEPT 5 EN 2 CARBOXYLIC ACID METHYL ESTER; CARBOXYLIC ACID DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; PHENYLGLYOXYLIC ACID; PROPANOIC ACID 1,2 BIS(2 METHOXYPHENYL) 2 (2 METHYLPROPOXY)ETHYL ESTER; PROPANOIC ACID 1,2 BIS(2 METHYLPHENYL) 2 (2 METHYLPROPOXY)ETHYL ESTER; PROPANOIC ACID 1,2 BIS(4 METHOXYPHENYL) 2 (2 METHYLPROPOXY)ETHYL ESTER; PROPANOIC ACID 2 (2 METHOXYETHOXY) 1,2 BIS(2 METHOXYPHENYL)ETHYL ESTER; PROPANOIC ACID 2 (2 METHOXYPROPOXY) 1,2 BIS [2 (TRIFLUOROMETHYL)PHENYL]ETHYL ESTER; PROPENOIC ACID 1,2 BIS(2 METHOXYPHENYL) 2 (2 METHYLPROPOXY)ETHYL ESTER; PROPENOIC ACID 2 (2 METHOXYETHOXY) 1,2 BIS(2 METHOXYPHENYL)ETHYL ESTER; PROPENOIC ACID 2 (2 METHOXYETHOXY) 1,2 DIPHENYLETHYL ESTER; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL MODEL; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 62849118755     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.02.004     Document Type: Article

References (94)

1. Gaertner P., Schuster C., and Knollmueller M. Lett. Org. Chem. 1 (2004) 249-253
2. Schuster C., Broeker J., Knollmueller M., and Gaertner P. Tetrahedron: Asymmetry 16 (2005) 2631-2647
3. Schuster C., Knollmueller M., and Gaertner P. Tetrahedron: Asymmetry 16 (2005) 3211-3223
4. Broeker J., Knollmueller M., and Gaertner P. Tetrahedron: Asymmetry 17 (2006) 2413-2429
5. Schuster C., Knollmueller M., and Gaertner P. Tetrahedron: Asymmetry 17 (2006) 2430-2441
6. For a recent review on polymer supported chiral auxiliaries see:. Chung C.W.Y., and Toy P.H. Tetrahedron: Asymmetry 15 (2004) 387-399
7. Noe C.R. Chem. Ber. 115 (1982) 1576-1590
8. Noe C.R., Knollmueller M., Wagner E., and Voellenkle H. Chem. Ber. 118 (1985) 1733-1745
9. Noe C.R., Knollmueller M., Steinbauer G., and Voellenkle H. Chem. Ber. 118 (1985) 4453-4458
10. Noe C.R., Knollmueller M., Steinbauer G., Jangg E., and Voellenkle H. Chem. Ber. 121 (1988) 1231-1239
11. Allin S.M., and Shuttleworth S.J. Tetrahedron Lett. 37 (1996) 8023-8026
12. Burgess K., and Lim D. Chem. Commun. (1997) 785-786
13. Purandare A.V., and Natarajan S. Tetrahedron Lett. 38 (1997) 8777-8780
14. Phoon C.W., and Abell C. Tetrahedron Lett. 39 (1998) 2655-2658
15. Winkler J.D., and McCoull W. Tetrahedron Lett. 39 (1998) 4935-4936
16. Faita G., Paio A., Quadrelli P., Rancati F., and Seneci P. Tetrahedron Lett. 41 (2000) 1265-1269
17. Bew S.P., Bull S.B., and Davies S.G. Tetrahedron Lett. 41 (2000) 7577-7581
18. Faita G., Paio A., Quadrelli P., Rancati F., and Seneci P. Tetrahedron 57 (2001) 8313-8322
19. Bew S.P., Bull S.B., Davies S.G., Savory E.D., and Watkin D.J. Tetrahedron 58 (2002) 9387-9401
20. Desimoni G., Faita G., Galbiati A., Pasini D., Quadrelli P., and Rancati F. Tetrahedron: Asymmetry 13 (2002) 333-337
21. Kotake T., Rajesh S., Hayashi Y., Mukai Y., Ueda M., Kimura T., and Kiso Y. Tetrahedron Lett. 45 (2004) 3651-3654
22. Allin S.M., Johnson C.A., and Timm A. Tetrahedron Lett. 46 (2005) 2495-2497
23. Davies S.G., Mortimer D.A.B., Mulvaney A.W., Russell A.J., Skarphedinsson H., Smith A.D., and Vickers R.J. Org. Biomol. Chem. 6 (2008) 1625-1634
24. Green R., Merritt A.T., and Bull S.T. Chem. Commun. (2008) 508-510
25. Sumrell G., Stevens J.I., and Goheen G.E. J. Org. Chem. 22 (1957) 39-41
26. Merz A., Gromann L., Karl A., Burgemeister T., and Kastner F. Liebigs Ann. Org. Bioorg. Chem. 10 (1996) 1635-1640
27. Deuchert K., Hertenstein U., Huenig S., and Wehner G. Chem. Ber. 112 (1979) 2045-2061
28. Huenig S., and Wehner G. Chem. Ber. 112 (1979) 2062-2067
29. Devant R., Mahler U., and Braun M. Chem. Ber. 121 (1988) 397-406
30. Sacha H., Waldmueller D., and Braun M. Chem. Ber. 127 (1994) 1959-1968
31. Larcheveque M., Ignatova E., and Cuvigny T. Tetrahedron Lett. 41 (1978) 3961-3964
32. Larcheveque M., Ignatova E., and Cuvigny T. J. Organomet. Chem. 177 (1979) 5-15
33. Evans D.A., and Takacs J.M. Tetrahedron Lett. 21 (1980) 4233-4236
34. Sonnet P.E., and Heath R.R. J. Org. Chem. 45 (1980) 3137-3139
35. Schmierer R., Grotemeier G., Helmchen G., and Selim A. Angew. Chem. 93 (1981) 209-210
36. Evans D.A., Ennis M.D., and Mathre D.J. J. Am. Chem. Soc. 104 (1982) 1737-1739
37. Kawanami Y., Ito Y., Kitagawa T., Taniguchi Y., Katsuki T., and Yamaguchi M. Tetrahedron Lett. 25 (1984) 857-860
38. Oppolzer W., Moretti R., and Thomi S. Tetrahedron Lett. 30 (1989) 5603-5606
39. Myers A.G., Yang B.H., Chen H., and Gleason J.L. J. Am. Chem. Soc. 116 (1994) 9361-9362
40. Myers A.G., Yang B.H., Chen H., McKinstry L., Kopecky D.J., and Gleason J.L. J. Am. Chem. Soc. 119 (1997) 6496-6511
41. Kishida M., Eguchi T., and Kakinuma K. Tetrahedron Lett. 37 (1996) 2061-2062
42. Mulzer J., Hiersemann M., Buschmann J., and Luger P. Liebigs Ann. (1996) 649-654
43. Tanner D., Birgersson C., and Gogoll A. Tetrahedron 50 (1994) 9797-9824
44. Evans M.D., and Kaye P.T. Synth. Commun. 31 (2001) 805-815
45. Davies S.G., Dixon D.J., Doisneau J.-M., Prodger J.C., and Sanganee H.J. Tetrahedron: Asymmetry 13 (2002) 647-658
46. Hutchison P.C., Heightman T.D., and Procter D.J. Org. Lett. 4 (2002) 4583-4585
47. Kerrigan N.J., Hutchison P.C., Heightman T.D., and Procter D.J. Chem. Commun. (2003) 1402-1403
48. Kotake T., Hayashi Y., Rajesh S., Mukai Y., Takiguchi Y., Kimura T., and Kiso Y. Tetrahedron 61 (2005) 3819-3834
49. Oppopzer W., Rodriguez I., Starkemann C., and Walther E. Tetrahedron Lett. 31 (1990) 5019-5022
50. Nerdel F., and Pawlowski K.H. Chem. Ber. 87 (1954) 215-217
51. Cavelier F., Gomez S., Jacquier R., Llinares M., Mercadier J.L., Petrus C., and Verducci J. Tetrahedron: Asymmetry 12 (1993) 2495-2500
52. Superchi S., Contursi M., and Rosini C. Tetrahedron 54 (1998) 11247-11254
53. Scafato P., Leo L., Superchi S., and Rosini C. Tetrahedron 58 (2002) 153-159
54. Rück-Braun K. In: Mulzer J., and Waldmann H. (Eds). Organic Synthesis Highlights III (1998), Wiley-VCH, Weinheim 13-22
55. Seebach D. Angew. Chem. 100 (1988) 1685-1715
56. Wipf P., and Stephenson C.R.J. Org. Lett. 5 (2003) 2449-2452
57. Koshiishi E., Hattori T., Ichihara N., and Miayano S. J. Chem. Soc., Perkin Trans. 1 (2002) 377-383
58. Loupy A., and Monteux D.A. Tetrahedron 58 (2002) 1541-1549
59. Senanayake C.H., Fang K., Grover P., Bakale R.P., Vandenbossche C.P., and Wals S.A. Tetrahedron Lett. 40 (1999) 819-822
60. Fukuzawa S.-I., Miura M., and Matsuzawa H. Tetrahedron Lett. 42 (2001) 4167-4169
61. Basavaiah D., Pandiaraju S., Bakthadoss M., and Muthukumaran K. Tetrahedron: Asymmetry 7 (1996) 997-1000
62. Basavaiah D., and Krishna P.R. Tetrahedron 51 (1995) 12169-12178
63. Comins D.L., Guerra-Weltzien L., and Salvador J.M. Synlett (1994) 972-974
64. Boireau G., Deberly A., and Abenhaim D. Tetrahedron 45 (1989) 5837-5844
65. Camps P., Font-Bardia M., Gimenez S., Perez F., Solans X., and Soldevilla N. Tetrahedron: Asymmetry 10 (1999) 3123-3138
66. Lait S.M., Parvez M., and Keay B.A. Tetrahedron: Asymmetry 14 (2003) 749-756
67. Burke M.J., Murray M.A., Parvez M., and Keay B.A. Tetrahedron: Asymmetry 11 (2000) 2733-2739
68. Kawamura M., and Kudo K. Chirality 14 (2002) 727-730
69. Mamedov E.G. Russ. J. Org. Chem. 37 (2001) 217-222
70. Nagatsuka T., Yamaguchi S., Totani K., Takao K., and Tadano K. Synlett (2001) 481-484
71. Enholm E.J., and Jiang S. J. Org. Chem. 65 (2000) 4756-4758
72. Sarakinos G., and Corey E.J. Org. Lett. 1 (1999) 1741-1744
73. Ito H., Saito A., and Taguchi T. Tetrahedron: Asymmetry 9 (1998) 1989-1994
74. Akiyama T., Horiguchi N., Ida T., and Ozaki S. Chem. Lett. 11 (1995) 975-976
75. Mathivanan P., and Maitra U. J. Org. Chem. 60 (1995) 364-369
76. Cipiciani A., Fringuelli F., Piermatti O., Pizzo F., and Ruzziconi R. J. Org. Chem. 67 (2002) 2665-2670
77. Kashima C., Fukusaka K., Takahashi K., and Yokoyama Y. J. Org. Chem. 64 (1999) 1108-1114
78. Chan W.H., Lee A.W.M., Jiang L.S., and Mak T.C.W. Tetrahedron: Asymmetry 8 (1997) 2501-2504
79. Le T.X.H., Bussolari J.C., and Murray W.V. Tetrahedron Lett. 38 (1997) 3849-3852
80. Avenoza A., Cativiela C., Paris M., and Peregrina J.M. Tetrahedron 52 (1996) 4839-4848
81. Banks M.R., Blake A.J., Cadogan J.I.G., Doyle A.A., Gosney I., Hodgson P.K.G., and Thorburn P. Tetrahedron 52 (1996) 4079-4094
82. Lakner F.J., and Negrete G.R. Synlett (2002) 643-645
83. Westwell A.D., and Williams J.M.J. Tetrahedron 53 (1997) 13063-13078
84. Evans D.A., Chapman K.T., and Bisaha J. J. Am. Chem. Soc. 110 (1988) 1238-1256
85. Corey E.J., Cheng X.-M., and Cimprich K.A. Tetrahedron Lett. 32 (1991) 6839-6842
86. Arehart S.V., and Pugh C. J. Am. Chem. Soc. 119 (1997) 3027-3037
87. Eda M., Takemoto T., Ono S., Okada T., Kosaka K., Gohda M., Matzno S., Nakamura N., and Fukaya C. J. Med. Chem. 37 (1994) 1983-1990
88. Angew. Chem. 96 (1984) 840-854
89. Worster P.M., McArthur C.R., and Leznoff C.C. Angew. Chem. 91 (1979) 255
90. McArthur C.R., Worster P.M., Jiang J.-L., and Leznoff C.C. Can. J. Chem. 60 (1982) 1836-1841
91. Akkari R., Calmes M., Escale F., Iapichella J., Rolland M., and Martinez J. Tetrahedron: Asymmetry 15 (2004) 2515-2525
92. Tyrrell E., Tsang M.W.H., Skinner G.A., and Fawcett J. Tetrahedron 52 (1996) 9841-9852
93. Watson S.C., and Eastham J.F. J. Organomet. Chem. 9 (1967) 165-168
94. Stammen B., Berlage U., Kindermann R., Kaiser M., Günther B., Sheldrick W.S., Welzel P., and Roth W.R. J. Org. Chem. 57 (1992) 6566-6575