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Chemistry - A European Journal

Volumn 11, Issue 1, 2005, Pages 330-343

New chiral auxiliaries for dynamic kinetic resolution: From theory to experiment

(4) Santos, A Gil a Pereira, Jorge a,b Afonso, Carlos A M c Frenking, Gernot d

a UNIVERSIDADE NOVA DE LISBOA (Portugal)

b INSTITUTO POLITÉCNICO DE SETÚBAL (Portugal)

c INSTITUTO SUPERIOR TÉCNICO (Portugal)

d PHILIPPS UNIVERSITY MARBURG (Germany)

Author keywords

Ab initio calculations; Asymmetric synthesis; Chiral auxiliaries; Kinetic resolution; Transition states

Indexed keywords

AMINES; ELECTRON TRANSITIONS; ELECTROSTATICS; HYDROGEN BONDS; ISOMERS; OPTICAL RESOLVING POWER; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CHIRAL AUXILIARIES; DYNAMIC KINETIC RESOLUTION (DKR); ELECTROSTATIC INTERACTIONS; ELECTROSTATIC REPULSION;

BROMINE COMPOUNDS;

IMIDAZOLE DERIVATIVE; OXAZOLIDINONE DERIVATIVE;

AB INITIO CALCULATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; ENERGY; HYDROGENATION; KINETICS; STEREOCHEMISTRY;

EID: 19944429372 PISSN: 09476539 EISSN: None Source Type: Journal
DOI: 10.1002/chem.200400512 Document Type: Article

Times cited : (22)

References (52)

1
- 0000021009
- I. Suzuki, H. Kin, Y. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10139-10146.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 10139-10146
- Suzuki, I.¹ Kin, H.² Yamamoto, Y.³

2
- 0029928212
- P. N. Devine, U.-H. Dolling, R. M. Heid, D. M. Tschaen, Tetrahedron Lett. 1996, 37, 2683-2686.
- (1996) Tetrahedron Lett. , vol.37 , pp. 2683-2686
- Devine, P.N.¹ Dolling, U.-H.² Heid, R.M.³ Tschaen, D.M.⁴

3
- 0000528934
- J. A. O'Meara, N. Gardee, M. Jung, R. N. Ben, T. Durst, J. Org. Chem. 1998, 63, 3117-3119.
- (1998) J. Org. Chem. , vol.63 , pp. 3117-3119
- O'Meara, J.A.¹ Gardee, N.² Jung, M.³ Ben, R.N.⁴ Durst, T.⁵

4
- 0343683426
- P. Camps, F. Pérez, N. Soldevilla, Tetrahedron: Asymmetry 1997, 8, 1877-1894.
- (1997) Tetrahedron: Asymmetry , vol.8 , pp. 1877-1894
- Camps, P.¹ Pérez, F.² Soldevilla, N.³

5
- 0345561581
- P. Camps, F. Pérez, N. Soldevilla, M. A. Borrego, Tetrahedron: Asymmetry 1999, 10, 493-509.
- (1999) Tetrahedron: Asymmetry , vol.10 , pp. 493-509
- Camps, P.¹ Pérez, F.² Soldevilla, N.³ Borrego, M.A.⁴

6
- 0028819296
- R. S. Ward, A. Pelter, D. Goubet, M. C. Pritchard, Tetrahedron: Asymmetry 1995, 6, 93-96.
- (1995) Tetrahedron: Asymmetry , vol.6 , pp. 93-96
- Ward, R.S.¹ Pelter, A.² Goubet, D.³ Pritchard, M.C.⁴

7
- 0028938839
- R. S. Ward, A. Pelter, D. Goubet, M. C. Pritchard, Tetrahedron: Asymmetry 1995, 6, 469-498.
- (1995) Tetrahedron: Asymmetry , vol.6 , pp. 469-498
- Ward, R.S.¹ Pelter, A.² Goubet, D.³ Pritchard, M.C.⁴

8
- 0025187520
- S. Hanessian, Y. L. Bennani, Tetrahedron Lett. 1990, 31, 6465-6468.
- (1990) Tetrahedron Lett. , vol.31 , pp. 6465-6468
- Hanessian, S.¹ Bennani, Y.L.²

9
- 0028857994
- V. J. Blazis, K. J. Koeller, C. D. Spilling, J. Org. Chem. 1995, 60, 931-937.
- (1995) J. Org. Chem. , vol.60 , pp. 931-937
- Blazis, V.J.¹ Koeller, K.J.² Spilling, C.D.³

10
- 0000959006
- H. Roder, G. Helmchen, E.-M. Peters, K. Peters, H.-G. Schnering, Angew. Chem. 1984, 96, 895-896; Angew. Chem. Int. Ed. Engl. 1984, 23, 898-899.
- (1984) Angew. Chem. , vol.96 , pp. 895-896
- Roder, H.¹ Helmchen, G.² Peters, E.-M.³ Peters, K.⁴ Schnering, H.-G.⁵

11
- 84985560842
- H. Roder, G. Helmchen, E.-M. Peters, K. Peters, H.-G. Schnering, Angew. Chem. 1984, 96, 895-896; Angew. Chem. Int. Ed. Engl. 1984, 23, 898-899.
- (1984) Angew. Chem. Int. Ed. Engl. , vol.23 , pp. 898-899

12
- 0012016624
- D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127-2129.
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 2127-2129
- Evans, D.A.¹ Bartroli, J.² Shih, T.L.³

13
- 33845554892
- D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737-1739.
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 1737-1739
- Evans, D.A.¹ Ennis, M.D.² Mathre, D.J.³

14
- 0002165370
- D. A. Evans, Aldrichimica Acta 1982, 15, 23-32.
- (1982) Aldrichimica Acta , vol.15 , pp. 23-32
- Evans, D.A.¹

15
- 0001594845
- D. A. Evans, M. M. Morrissey, R. L. Dorow, J. Am. Chem. Soc. 1985, 107, 4346-4348.
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 4346-4348
- Evans, D.A.¹ Morrissey, M.M.² Dorow, R.L.³

16
- 0028130661
- I. Abrahams, M. Motevalli, A. J. Robinson, P. B. Wyatt, Tetrahedron 1994, 50, 12755-12772.
- (1994) Tetrahedron , vol.50 , pp. 12755-12772
- Abrahams, I.¹ Motevalli, M.² Robinson, A.J.³ Wyatt, P.B.⁴

17
- 0001182561
- A. Abdel-Magid, L. N. Pridgen, D. S. Eggleston, I. Lantos, J. Am. Chem. Soc. 1986, 108, 4595-4602.
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 4595-4602
- Abdel-Magid, A.¹ Pridgen, L.N.² Eggleston, D.S.³ Lantos, I.⁴

18
- 0022490196
- D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1986, 108, 6757-6761.
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 6757-6761
- Evans, D.A.¹ Weber, A.E.²

19
- 33845280186
- D. A. Evans, K. T. Chapman, J. Bisaba, J. Am. Chem. Soc. 1988, 110, 1238-1256.
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 1238-1256
- Evans, D.A.¹ Chapman, K.T.² Bisaba, J.³

20
- 0035939150
- A. G. Santos, S. X. Candeias, C. A. M. Afonso, K. Jenkins, S. Caddick, N. R. Treweeke, D. Pardoe, Tetrahedron 2001, 57, 6607-6614.
- (2001) Tetrahedron , vol.57 , pp. 6607-6614
- Santos, A.G.¹ Candeias, S.X.² Afonso, C.A.M.³ Jenkins, K.⁴ Caddick, S.⁵ Treweeke, N.R.⁶ Pardoe, D.⁷

21
- 0035912361
- G. Cardillo, L. Gentilucci, M. Gianotti, A. Tolomelli, Org. Lett. 2001, 3, 1165-1167.
- (2001) Org. Lett. , vol.3 , pp. 1165-1167
- Cardillo, G.¹ Gentilucci, L.² Gianotti, M.³ Tolomelli, A.⁴

22
- 0027723315
- E. Nicolás, K. C. Rüssel, J. Knollenberg, V. J. Hruby, J. Org. Chem. 1993, 58, 7565-7571.
- (1993) J. Org. Chem. , vol.58 , pp. 7565-7571
- Nicolás, E.¹ Rüssel, K.C.² Knollenberg, J.³ Hruby, V.J.⁴

23
- 0027411466
- G. Li, M. A. Jarosinski, V. J. Hruby, Tetrahedron Lett. 1993, 34, 2561-2564.
- (1993) Tetrahedron Lett. , vol.34 , pp. 2561-2564
- Li, G.¹ Jarosinski, M.A.² Hruby, V.J.³

24
- 0030025106
- K. J. Hale, J. Cai, V. Delisser, S. Manaviazar, S. A. Peak, G. S. Bhatia, T. C. Collins, N. Jogiya, Tetrahedron 1996, 52, 1047-1068.
- (1996) Tetrahedron , vol.52 , pp. 1047-1068
- Hale, K.J.¹ Cai, J.² Delisser, V.³ Manaviazar, S.⁴ Peak, S.A.⁵ Bhatia, G.S.⁶ Collins, T.C.⁷ Jogiya, N.⁸

25
- 0000822037
- J. H. Wu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11029-11030.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 11029-11030
- Wu, J.H.¹ Radinov, R.² Porter, N.A.³

26
- 0029814298
- M. P. Sibi, J. Ji, J. Org. Chem. 1996, 61, 6090-6091.
- (1996) J. Org. Chem. , vol.61 , pp. 6090-6091
- Sibi, M.P.¹ Ji, J.²

27
- 0000263079
- M. P. Sibi, C. P. Jasperse, J. Ji, J. Am. Chem. Soc. 1995, 117, 10779-10780.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 10779-10780
- Sibi, M.P.¹ Jasperse, C.P.² Ji, J.³

28
- 0029804421
- M. P. Sibi, J. Ji, J. Am. Chem. Soc. 1996, 118, 9200-9201.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 9200-9201
- Sibi, M.P.¹ Ji, J.²

29
- 0028198198
- Y. Yamamoto, S. Onuki, M. Yumoto, N. Asao, J. Am. Chem. Soc. 1994, 116, 421-422.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 421-422
- Yamamoto, Y.¹ Onuki, S.² Yumoto, M.³ Asao, N.⁴

30
- 0033538275
- C. L. Mero, N. A. Porter, J. Am. Chem. Soc. 1999, 121, 5155-5160.
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 5155-5160
- Mero, C.L.¹ Porter, N.A.²

31
- 0033556602
- For reviews in DKR, see: a) U. T. Strauss, U. Felfer, K. Faber, Tetrahedron: Asymmetry 1999, 10, 107-117;
- (1999) Tetrahedron: Asymmetry , vol.10 , pp. 107-117
- Strauss, U.T.¹ Felfer, U.² Faber, K.³

32
- 0030342797
- b) S. Caddick, K. Jenkins, Chem. Soc. Rev. 1996, 25, 447-456;
- (1996) Chem. Soc. Rev. , vol.25 , pp. 447-456
- Caddick, S.¹ Jenkins, K.²

33
- 0029103383
- c) R. S. Ward, Tetrahedron: Asymmetry 1995, 6, 1475-1490;
- (1995) Tetrahedron: Asymmetry , vol.6 , pp. 1475-1490
- Ward, R.S.¹

34
- 0002923489
- d) R. Noyori, M. Tokunaga, M. Kitamura, Bull. Chem. Soc. Jpn. 1995, 68, 36-56.
- (1995) Bull. Chem. Soc. Jpn. , vol.68 , pp. 36-56
- Noyori, R.¹ Tokunaga, M.² Kitamura, M.³

35
- 0030023044
- S. Caddick, S. Jenkins, Tetrahedron Lett. 1996, 37, 1301-1304.
- (1996) Tetrahedron Lett. , vol.37 , pp. 1301-1304
- Caddick, S.¹ Jenkins, S.²

36
- 0032499048
- S. Caddick, S. Jenkins, N. Treweeke, S. X. Candeias, C. A. Afonso, Tetrahedron Lett. 1998, 39, 2203-2206.
- (1998) Tetrahedron Lett. , vol.39 , pp. 2203-2206
- Caddick, S.¹ Jenkins, S.² Treweeke, N.³ Candeias, S.X.⁴ Afonso, C.A.⁵

37
- 0028954208
- J. A. O'Meara, M. Jung, T. Durst, Tetrahedron Lett. 1995, 36, 2559-2562.
- (1995) Tetrahedron Lett. , vol.36 , pp. 2559-2562
- O'Meara, J.A.¹ Jung, M.² Durst, T.³

38
- 0028228733
- H. Kubota, A. Kubo, K. Nunami, Tetrahedron Lett. 1994, 35, 3107-3110.
- (1994) Tetrahedron Lett. , vol.35 , pp. 3107-3110
- Kubota, H.¹ Kubo, A.² Nunami, K.³

39
- 0028019369
- K. Nunami, H. Kubota, A. Kubo, Tetrahedron Lett. 1994, 35, 8639-8642.
- (1994) Tetrahedron Lett. , vol.35 , pp. 8639-8642
- Nunami, K.¹ Kubota, H.² Kubo, A.³

40
- 0000308076
- H. Kubota, A. Kubo, M. Takahashi, R. Shimizu, T. Da-te, K. Okamura, K. Nunami, J. Org. Chem. 1995, 60, 6776-6784.
- (1995) J. Org. Chem. , vol.60 , pp. 6776-6784
- Kubota, H.¹ Kubo, A.² Takahashi, M.³ Shimizu, R.⁴ Da-Te, T.⁵ Okamura, K.⁶ Nunami, K.⁷

41
- 0029161697
- A. Kubo, M. Takahashi, H. Kubota, K. Nunami, Tetrahedron Lett. 1995, 36, 6251-6252.
- (1995) Tetrahedron Lett. , vol.36 , pp. 6251-6252
- Kubo, A.¹ Takahashi, M.² Kubota, H.³ Nunami, K.⁴

42
- 0000863030
- A. Kubo, H. Kubota, M. Takahashi, K. Nunami, K. Tetrahedron Lett. 1996, 37, 4957-4960.
- (1996) Tetrahedron Lett. , vol.37 , pp. 4957-4960
- Kubo, A.¹ Kubota, H.² Takahashi, M.³ Nunami, K.⁴

43
- 0001365258
- A. Kubo, H. Kubota, M. Takahashi, K. Nunami, J. Org. Chem. 1997, 62, 5830-5837.
- (1997) J. Org. Chem. , vol.62 , pp. 5830-5837
- Kubo, A.¹ Kubota, H.² Takahashi, M.³ Nunami, K.⁴

44
- 0033523087
- J. Clariana, N. Gálvez, C. Marchi, M. Moreno-Mañas, A. Vallribera, E. Molins, Tetrahedron 1999, 55, 7331-7344.
- (1999) Tetrahedron , vol.55 , pp. 7331-7344
- Clariana, J.¹ Gálvez, N.² Marchi, C.³ Moreno-Mañas, M.⁴ Vallribera, A.⁵ Molins, E.⁶

45
- 17844393636
- S. Caddick, C. A. M. Afonso, S. X. Candeias, P. B. Hitchcock, K. Jenkins, L. Murtagh, D. Pardoe, A. G. Santos, N. R. Treweeke, R. Weaving, Tetrahedron 2001, 57, 6589-6605.
- (2001) Tetrahedron , vol.57 , pp. 6589-6605
- Caddick, S.¹ Afonso, C.A.M.² Candeias, S.X.³ Hitchcock, P.B.⁴ Jenkins, K.⁵ Murtagh, L.⁶ Pardoe, D.⁷ Santos, A.G.⁸ Treweeke, N.R.⁹ Weaving, R.¹⁰

46
- 84873082077
- Wavefunction, Inc. Irvine, CA
- Spartan '02, Wavefunction, Inc. Irvine, CA.
- Spartan '02

47
- 0004133516
- Gaussian, Inc., Pittsburgh PA
- Gaussian 98, Revision A.7, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1998.
- (1998) Gaussian 98, Revision A.7
- Frisch, M.J.¹ Trucks, G.W.² Schlegel, H.B.³ Scuseria, G.E.⁴ Robb, M.A.⁵ Cheeseman, J.R.⁶ Zakrzewski, V.G.⁷ Montgomery Jr., J.A.⁸ Stratmann, R.E.⁹ Burant, J.C.¹⁰ Dapprich, S.¹¹ Millam, J.M.¹² Daniels, A.D.¹³ Kudin, K.N.¹⁴ Strain, M.C.¹⁵ Farkas, O.¹⁶ Tomasi, J.¹⁷ Barone, V.¹⁸ Cossi, M.¹⁹ Cammi, R.²⁰ more..

48
- 0035281210
- S. Tsuzuki, H. P. J. Lüthi, Chem. Phys. 2091, 114, 3949-3957.
- Chem. Phys. , vol.114 , pp. 3949-3957
- Tsuzuki, S.¹ Lüthi, H.P.J.²

49
- 0034614545
- F. Moreau, D. Florentin, A. Marquet, Tetrahedron 2000, 56, 285-293.
- (2000) Tetrahedron , vol.56 , pp. 285-293
- Moreau, F.¹ Florentin, D.² Marquet, A.³

50
- 0034815665
- S. X. Candeias, K. Jenkins, C. A. M. Afonso, S. Caddick, Synth. Commun. 2001, 31, 3241-3254.
- (2001) Synth. Commun. , vol.31 , pp. 3241-3254
- Candeias, S.X.¹ Jenkins, K.² Afonso, C.A.M.³ Caddick, S.⁴

51
- 0016613731
- N. Finch, J. J. Fitt, I. H. S. Hsu, J. Org. Chem. 1975, 40, 206-215.
- (1975) J. Org. Chem. , vol.40 , pp. 206-215
- Finch, N.¹ Fitt, J.J.² Hsu, I.H.S.³

52
- 0024521183
- K. Hayashi, K. Nunami, J. Kato, N. Yoneda, M. Kubo, T. Ochiai, R. Ishida, Med. Chem. 1989, 32, 289-297.
- (1989) Med. Chem. , vol.32 , pp. 289-297
- Hayashi, K.¹ Nunami, K.² Kato, J.³ Yoneda, N.⁴ Kubo, M.⁵ Ochiai, T.⁶ Ishida, R.⁷

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