-
1
-
-
33947361092
-
-
Zhang Y., Fechter E.J., Wang T.-S.A., Barrett D., Walker S., and Kahne D.E. J. Am. Chem. Soc. 129 (2007) 3080
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 3080
-
-
Zhang, Y.1
Fechter, E.J.2
Wang, T.-S.A.3
Barrett, D.4
Walker, S.5
Kahne, D.E.6
-
2
-
-
34548541005
-
-
Yamawaki K., Nomura T., Yasukata T., Uotani K., Miwa H., Takeda K., and Nishitani Y. Bioorg. Med. Chem. 15 (2007) 6716
-
(2007)
Bioorg. Med. Chem.
, vol.15
, pp. 6716
-
-
Yamawaki, K.1
Nomura, T.2
Yasukata, T.3
Uotani, K.4
Miwa, H.5
Takeda, K.6
Nishitani, Y.7
-
3
-
-
28844507959
-
-
Liakatos A., Kiefel M.J., Fleming F., Coulson B., and von Itzstein M. Bioorg. Med. Chem. 14 (2006) 739
-
(2006)
Bioorg. Med. Chem.
, vol.14
, pp. 739
-
-
Liakatos, A.1
Kiefel, M.J.2
Fleming, F.3
Coulson, B.4
von Itzstein, M.5
-
4
-
-
0037030644
-
-
Yuan Z., Blomberg D., Sethson I., Brickmann K., Ekholm K., Johansson B., Nilsson A., and Kihlberg J. J. Med. Chem. 45 (2002) 2512
-
(2002)
J. Med. Chem.
, vol.45
, pp. 2512
-
-
Yuan, Z.1
Blomberg, D.2
Sethson, I.3
Brickmann, K.4
Ekholm, K.5
Johansson, B.6
Nilsson, A.7
Kihlberg, J.8
-
5
-
-
0036279986
-
-
Fujisawa T., Igeta K., Odake S., Morita Y., Yasuda J., and Morikawa T. Bioorg. Med. Chem. 10 (2002) 2569
-
(2002)
Bioorg. Med. Chem.
, vol.10
, pp. 2569
-
-
Fujisawa, T.1
Igeta, K.2
Odake, S.3
Morita, Y.4
Yasuda, J.5
Morikawa, T.6
-
7
-
-
38149094270
-
-
Deaton D.N., Gao E.N., Graham K.P., Gross J.W., Miller A.B., and Strelow J.M. Bioorg. Med. Chem. Lett. 18 (2008) 732
-
(2008)
Bioorg. Med. Chem. Lett.
, vol.18
, pp. 732
-
-
Deaton, D.N.1
Gao, E.N.2
Graham, K.P.3
Gross, J.W.4
Miller, A.B.5
Strelow, J.M.6
-
9
-
-
0344527755
-
-
Souers A.J., Schuerer S., Kwack H., Virgilio A.A., and Ellman J.A. Synthesis (1999) 583
-
(1999)
Synthesis
, pp. 583
-
-
Souers, A.J.1
Schuerer, S.2
Kwack, H.3
Virgilio, A.A.4
Ellman, J.A.5
-
10
-
-
72049109882
-
-
note
-
It has been proposed that the epimerization of α-halo carbon center is promoted via the nucleophilic displacement of the halide ion and/or base-catalyzed keto-enol tautomerization process.
-
-
-
-
12
-
-
0033623224
-
-
Beak P., Anderson D.R., Curtis M.D., Laumer J.M., Pippel D.J., and Weisenburger G.A. Acc. Chem. Res. 33 (2000) 715
-
(2000)
Acc. Chem. Res.
, vol.33
, pp. 715
-
-
Beak, P.1
Anderson, D.R.2
Curtis, M.D.3
Laumer, J.M.4
Pippel, D.J.5
Weisenburger, G.A.6
-
18
-
-
27944472739
-
-
When chiral auxiliary bound α-halo acid derivative 1 was prepared from racemic α-halo carboxylic acid, we might expect to obtain a 1:1 diastereomeric mixture of 1. In some cases, however, the formation of anything other than a 1:1 mixture of diastereomers is observed, which can be explained by dynamic resolution in the ester or amide bond formation reaction. Also, the in situ preparation of a ketene from α-halo acid halides and its asymmetric reaction with a chiral auxiliary can afford α-halo esters or amides with high stereoselectivities:
-
When chiral auxiliary bound α-halo acid derivative 1 was prepared from racemic α-halo carboxylic acid, we might expect to obtain a 1:1 diastereomeric mixture of 1. In some cases, however, the formation of anything other than a 1:1 mixture of diastereomers is observed, which can be explained by dynamic resolution in the ester or amide bond formation reaction. Also, the in situ preparation of a ketene from α-halo acid halides and its asymmetric reaction with a chiral auxiliary can afford α-halo esters or amides with high stereoselectivities:. Boschi F., Camps P., Comes-Franchini M., Muňoz-Torrero D., Ricci A., and Sánchez L. Tetrahedron: Asymmetry 16 (2005) 3739
-
(2005)
Tetrahedron: Asymmetry
, vol.16
, pp. 3739
-
-
Boschi, F.1
Camps, P.2
Comes-Franchini, M.3
Muňoz-Torrero, D.4
Ricci, A.5
Sánchez, L.6
-
19
-
-
1042275590
-
-
Cardillo G., Fabbroni S., Gentilucci L., Perciaccante R., and Tolomelli A. Tetrahedron: Asymmetry 15 (2004) 593
-
(2004)
Tetrahedron: Asymmetry
, vol.15
, pp. 593
-
-
Cardillo, G.1
Fabbroni, S.2
Gentilucci, L.3
Perciaccante, R.4
Tolomelli, A.5
-
27
-
-
33847338943
-
-
Kim Y., Kang K.H., Choi E.T., Lee M.H., and Park Y.S. Bull. Korean Chem. Soc. 28 (2007) 325
-
(2007)
Bull. Korean Chem. Soc.
, vol.28
, pp. 325
-
-
Kim, Y.1
Kang, K.H.2
Choi, E.T.3
Lee, M.H.4
Park, Y.S.5
-
28
-
-
72049125013
-
-
We have performed molecular mechanics calculations (MMC) with the InsightII/Discover program using consistent valence force field, unpublished results.
-
We have performed molecular mechanics calculations (MMC) with the InsightII/Discover program using consistent valence force field, unpublished results.
-
-
-
-
31
-
-
45149119180
-
-
Lee M.H., Kang K.H., Lee Y.M., Kim D., and Park Y.S. Bull. Korean Chem. Soc. 29 (2008) 1075
-
(2008)
Bull. Korean Chem. Soc.
, vol.29
, pp. 1075
-
-
Lee, M.H.1
Kang, K.H.2
Lee, Y.M.3
Kim, D.4
Park, Y.S.5
-
32
-
-
2942525761
-
-
Kiau S., Discordia R.P., Madding G., Okuniewicz F.J., Rosso V., and Venit J.J. J. Org. Chem. 69 (2004) 4256
-
(2004)
J. Org. Chem.
, vol.69
, pp. 4256
-
-
Kiau, S.1
Discordia, R.P.2
Madding, G.3
Okuniewicz, F.J.4
Rosso, V.5
Venit, J.J.6
-
33
-
-
4644327960
-
-
Chen J.G., Zhu J., Skonezny P.M., Rosso V., and Venit J.J. Org. Lett. 6 (2004) 3233
-
(2004)
Org. Lett.
, vol.6
, pp. 3233
-
-
Chen, J.G.1
Zhu, J.2
Skonezny, P.M.3
Rosso, V.4
Venit, J.J.5
-
37
-
-
0000528934
-
-
O′Meara J.A., Gardee N., Jung M., Ben R.N., and Durst T. J. Org. Chem. 63 (1998) 3117
-
(1998)
J. Org. Chem.
, vol.63
, pp. 3117
-
-
OMeara, J.A.1
Gardee, N.2
Jung, M.3
Ben, R.N.4
Durst, T.5
-
42
-
-
18944373681
-
-
Kim H.J., Shin E.-K., Chang J.-Y., Kim Y., and Park Y.S. Tetrahedron Lett. 46 (2005) 4115
-
(2005)
Tetrahedron Lett.
, vol.46
, pp. 4115
-
-
Kim, H.J.1
Shin, E.-K.2
Chang, J.-Y.3
Kim, Y.4
Park, Y.S.5
-
43
-
-
33646758906
-
-
Kim H.J., Kim Y., Choi E.T., Lee M.H., No E.S., and Park Y.S. Tetrahedron 62 (2006) 6303
-
(2006)
Tetrahedron
, vol.62
, pp. 6303
-
-
Kim, H.J.1
Kim, Y.2
Choi, E.T.3
Lee, M.H.4
No, E.S.5
Park, Y.S.6
-
44
-
-
33847383365
-
-
Kim Y., Lee M.H., Choi E.T., No E.S., and Park Y.S. Heterocycles 71 (2007) 5
-
(2007)
Heterocycles
, vol.71
, pp. 5
-
-
Kim, Y.1
Lee, M.H.2
Choi, E.T.3
No, E.S.4
Park, Y.S.5
-
49
-
-
33748769245
-
-
Ammazzalorso A., Amoroso R., Bettoni G., De Filippis B., Giampietro L., Maccallini C., and Tricca M.L. Arkivoc (2004) 375
-
(2004)
Arkivoc
, pp. 375
-
-
Ammazzalorso, A.1
Amoroso, R.2
Bettoni, G.3
De Filippis, B.4
Giampietro, L.5
Maccallini, C.6
Tricca, M.L.7
-
50
-
-
33748786287
-
-
Ammazzalorso A., Amoroso R., Bettoni G., De Filippis B., Fantacuzzi M., Giampietro L., Maccallini C., and Tricca M.L. Eur. J. Org. Chem. (2006) 4088
-
(2006)
Eur. J. Org. Chem.
, pp. 4088
-
-
Ammazzalorso, A.1
Amoroso, R.2
Bettoni, G.3
De Filippis, B.4
Fantacuzzi, M.5
Giampietro, L.6
Maccallini, C.7
Tricca, M.L.8
-
53
-
-
0000308076
-
-
Kubota H., Kubo A., Takahashi M., Shimizu R., Da-te T., Okamura K., and Nunami K.-i. J. Org. Chem. 60 (1995) 6776
-
(1995)
J. Org. Chem.
, vol.60
, pp. 6776
-
-
Kubota, H.1
Kubo, A.2
Takahashi, M.3
Shimizu, R.4
Da-te, T.5
Okamura, K.6
Nunami, K.-i.7
-
57
-
-
0032499048
-
-
Caddick S., Jenkins K., Treweeke N., Candeias S.X., and Afonso C.A.M. Tetrahedron Lett. 39 (1998) 2203
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 2203
-
-
Caddick, S.1
Jenkins, K.2
Treweeke, N.3
Candeias, S.X.4
Afonso, C.A.M.5
-
58
-
-
17844393636
-
-
Caddick S., Afonso C.A.M., Candeias S.X., Hitchcock P.B., Jenkins K., Murtagh L., Pardoe D., Santos A.G., Treweeke N.R., and Weaving R. Tetrahedron 57 (2001) 6589
-
(2001)
Tetrahedron
, vol.57
, pp. 6589
-
-
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
-
59
-
-
0035939150
-
-
Santos A.G., Candeias S.X., Afonso C.A.M., Jenkins K., Caddick S., Treweeke N.R., and Pardoe D. Tetrahedron 57 (2001) 6607
-
(2001)
Tetrahedron
, vol.57
, pp. 6607
-
-
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
-
65
-
-
3242785709
-
-
Nam J., Chang J.-Y., Shin E.-K., Kim H.J., Kim Y., Jang S., and Park Y.S. Tetrahedron 60 (2004) 6311
-
(2004)
Tetrahedron
, vol.60
, pp. 6311
-
-
Nam, J.1
Chang, J.-Y.2
Shin, E.-K.3
Kim, H.J.4
Kim, Y.5
Jang, S.6
Park, Y.S.7
-
66
-
-
14344255552
-
-
Chang J.-Y., Shin E.-K., Kim H.J., Kim Y., and Park Y.S. Tetrahedron 61 (2005) 2743
-
(2005)
Tetrahedron
, vol.61
, pp. 2743
-
-
Chang, J.-Y.1
Shin, E.-K.2
Kim, H.J.3
Kim, Y.4
Park, Y.S.5
-
68
-
-
22744457639
-
-
Chang J.-Y., Shin E.-K., Kim H.J., Kim Y., and Park Y.S. Bull. Korean Chem. Soc. 26 (2005) 989
-
(2005)
Bull. Korean Chem. Soc.
, vol.26
, pp. 989
-
-
Chang, J.-Y.1
Shin, E.-K.2
Kim, H.J.3
Kim, Y.4
Park, Y.S.5
-
69
-
-
33645216187
-
-
Shin E.-K., Chang J.-Y., Kim H.J., Kim Y., and Park Y.S. Bull. Korean Chem. Soc. 27 (2006) 447
-
(2006)
Bull. Korean Chem. Soc.
, vol.27
, pp. 447
-
-
Shin, E.-K.1
Chang, J.-Y.2
Kim, H.J.3
Kim, Y.4
Park, Y.S.5
|