-
6
-
-
23944488828
-
-
Tsogoeva S.B., Hately M.J., Yalalov D.A., Meindl K., Weckbecker C., and Huthmacher K. Bioorg. Med. Chem. 13 (2005) 5680-5685
-
(2005)
Bioorg. Med. Chem.
, vol.13
, pp. 5680-5685
-
-
Tsogoeva, S.B.1
Hately, M.J.2
Yalalov, D.A.3
Meindl, K.4
Weckbecker, C.5
Huthmacher, K.6
-
7
-
-
28444495969
-
-
Tsogoeva S.B., Yalalov D.A., Hately M.J., Weckbecker C., and Huthmacher K. Eur. J. Org. Chem. (2005) 4995-5000
-
(2005)
Eur. J. Org. Chem.
, pp. 4995-5000
-
-
Tsogoeva, S.B.1
Yalalov, D.A.2
Hately, M.J.3
Weckbecker, C.4
Huthmacher, K.5
-
11
-
-
28944450864
-
-
Hoashi Y., Yabuta T., Yuan P., Miyabe H., and Takemoto Y. Tetrahedron 62 (2006) 365-374
-
(2006)
Tetrahedron
, vol.62
, pp. 365-374
-
-
Hoashi, Y.1
Yabuta, T.2
Yuan, P.3
Miyabe, H.4
Takemoto, Y.5
-
13
-
-
11844302258
-
-
Okino T., Hoashi Y., Furukawa T., Xuenong X., and Takemoto Y. J. Am. Chem. Soc. 127 (2005) 119-125
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 119-125
-
-
Okino, T.1
Hoashi, Y.2
Furukawa, T.3
Xuenong, X.4
Takemoto, Y.5
-
16
-
-
27144522622
-
-
Wang J., Li H., Duan W., Zu L., and Wang W. Org. Lett. 7 (2005) 4713-4716
-
(2005)
Org. Lett.
, vol.7
, pp. 4713-4716
-
-
Wang, J.1
Li, H.2
Duan, W.3
Zu, L.4
Wang, W.5
-
19
-
-
15444366940
-
-
Li B., Jiang L., Liu M., Chen Y., Ding L., and Wu Y. Synlett (2005) 603-606
-
(2005)
Synlett
, pp. 603-606
-
-
Li, B.1
Jiang, L.2
Liu, M.3
Chen, Y.4
Ding, L.5
Wu, Y.6
-
20
-
-
28444495969
-
-
Tsogoeva S.B., Yalalov D.A., Hately M.J., Weckbecker C., and Huthmacher K. Eur. J. Org. Chem. (2005) 4995-5000
-
(2005)
Eur. J. Org. Chem.
, pp. 4995-5000
-
-
Tsogoeva, S.B.1
Yalalov, D.A.2
Hately, M.J.3
Weckbecker, C.4
Huthmacher, K.5
-
21
-
-
25444432564
-
-
Wang J., Li H., Yu X., Zu L., and Wang W. Org. Lett. 7 (2005) 4293-4296
-
(2005)
Org. Lett.
, vol.7
, pp. 4293-4296
-
-
Wang, J.1
Li, H.2
Yu, X.3
Zu, L.4
Wang, W.5
-
27
-
-
32044463560
-
-
Marcelli T., van der Haas R.N.S., van Maarseveen J.H., and Hiemstra H. Angew. Chem., Int. Ed. 45 (2006) 929-931
-
(2006)
Angew. Chem., Int. Ed.
, vol.45
, pp. 929-931
-
-
Marcelli, T.1
van der Haas, R.N.S.2
van Maarseveen, J.H.3
Hiemstra, H.4
-
28
-
-
30544439939
-
-
Sohtome Y., Takemura N., Iguchi T., Yuichi H., and Nagasawa K. Synlett (2006) 144-146
-
(2006)
Synlett
, pp. 144-146
-
-
Sohtome, Y.1
Takemura, N.2
Iguchi, T.3
Yuichi, H.4
Nagasawa, K.5
-
30
-
-
28944454980
-
-
Bernardi L., Fini F., Herrera R.P., Ricci A., and Sgarzini V. Tetrahedron 62 (2006) 375-380
-
(2006)
Tetrahedron
, vol.62
, pp. 375-380
-
-
Bernardi, L.1
Fini, F.2
Herrera, R.P.3
Ricci, A.4
Sgarzini, V.5
-
31
-
-
29544439946
-
-
Xu X., Furukawa T., Okino T., Miyabe H., and Takemoto Y. Chem. Eur. J. 12 (2006) 466-476
-
(2006)
Chem. Eur. J.
, vol.12
, pp. 466-476
-
-
Xu, X.1
Furukawa, T.2
Okino, T.3
Miyabe, H.4
Takemoto, Y.5
-
37
-
-
0001678717
-
-
Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds), Springer, Berlin
-
Mori A., and Inoue S. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. 2 (1999), Springer, Berlin 983-994
-
(1999)
Comprehensive Asymmetric Catalysis
, vol.2
, pp. 983-994
-
-
Mori, A.1
Inoue, S.2
-
44
-
-
27544472739
-
-
Kitani Y., Kumamoto T., Isobe T., Fukada K., and Ishikawa T. Adv. Synth. Catal. 347 (2005) 1653-1658
-
(2005)
Adv. Synth. Catal.
, vol.347
, pp. 1653-1658
-
-
Kitani, Y.1
Kumamoto, T.2
Isobe, T.3
Fukada, K.4
Ishikawa, T.5
-
46
-
-
26844570657
-
-
Wen Y., Huang X., Huang J., Xiong Y., Qin B., and Feng X. Synlett (2005) 2445-2448
-
(2005)
Synlett
, pp. 2445-2448
-
-
Wen, Y.1
Huang, X.2
Huang, J.3
Xiong, Y.4
Qin, B.5
Feng, X.6
-
48
-
-
33646479607
-
-
Vanthuyne N., Andreoli F., Fernandez S., Roman M., and Roussel C. Lett. Org. Chem. 2 (2005) 433-443
-
(2005)
Lett. Org. Chem.
, vol.2
, pp. 433-443
-
-
Vanthuyne, N.1
Andreoli, F.2
Fernandez, S.3
Roman, M.4
Roussel, C.5
-
49
-
-
33646471220
-
-
note
-
It is clear that the results obtained using the single diastereomer (aR)-(S,S)-1 are the same as would be obtained using the single diastereomer (aS)-(R,R)-1: as in fact the two catalysts are enantiomers, the opposite absolute configuration of the reaction product is obtained, but with the same yield and ee. For this reason, we can conclude that the mixture (aR/aS)-(R,R)-1 (which gives (S)-2-hydroxy-2-phenylacetonitrile in quantitative yield and 66.3% ee) performs better than the two separated diastereomers, (aR)-(R,R)-1 [which gives (S)-2-hydroxy-2-phenylacetonitrile in 30% yield and 46.7% ee] and (aS)-(R,R)-1 (which gives (S)-2-hydroxy-2-phenylacetonitrile in quantitative yield and 55.0% ee, as inferred from the experiment with its enantiomer (aR)-(S,S)-1, which gives (R)-2-hydroxy-2-phenylacetonitrile in quantitative yield and 55.0% ee).
-
-
-
-
50
-
-
33646473199
-
-
note
-
Both the single diastereomers (aR)-(R,R)-1, (aR)-(S,S)-1 and the mixture (aR/aS)-(R,R)-1 are completely soluble in the reaction mixture (0.04 M in dichloromethane at -20 °C). Therefore, the enhanced performance of the mixture of the diastereomers compared to the single diastereomers alone cannot be explained in terms of their different solubility in the reaction medium.
-
-
-
-
51
-
-
33646492999
-
-
note
-
The involvement of a dimeric organocatalyst was proposed for explaining the kinetics of cyanohydrin formation catalysed by the cyclic dipeptide cyclo[(R)-His-(R)-Phe], see Ref. 11a and references therein.
-
-
-
-
57
-
-
0036090892
-
-
Veum L., Kuster M., Telalovic S., Hanefeld U., and Maschmeyer T. Eur. J. Org. Chem. (2002) 1516-1522
-
(2002)
Eur. J. Org. Chem.
, pp. 1516-1522
-
-
Veum, L.1
Kuster, M.2
Telalovic, S.3
Hanefeld, U.4
Maschmeyer, T.5
|