-
1
-
-
72249102189
-
-
For recent reviews on enzymes in organic chemistry, see:
-
For recent reviews on enzymes in organic chemistry, see:, Suga T, Curr. Org. Chem. 1999 3 377
-
(1999)
Curr. Org. Chem.
, vol.3
, pp. 377
-
-
Suga, T.1
-
5
-
-
4143054678
-
-
For recent reviews on organocatalysts, see:
-
For recent reviews on organocatalysts, see:, Ooi T, Maruoka K, Acc. Chem. Res. 2004 37 526
-
(2004)
Acc. Chem. Res.
, vol.37
, pp. 526
-
-
Ooi, T.1
Maruoka, K.2
-
6
-
-
4143136647
-
-
Tian S.-K, Chen Y, Hang J, Tang L, McDaid P, Deng L, Acc. Chem. Res. 2004 37 621
-
(2004)
Acc. Chem. Res.
, vol.37
, pp. 621
-
-
Tian, S.-K.1
Chen, Y.2
Hang, J.3
Tang, L.4
McDaid, P.5
Deng, L.6
-
10
-
-
33845766272
-
-
Gaunt M J., Johansson C C. C., McNally A, Vo N T., Drug Discovery Today 2006 12 8
-
(2006)
Drug Discovery Today
, vol.12
, pp. 8
-
-
Gaunt, M.J.1
Johansson, C.C.C.2
McNally, A.3
Vo, N.T.4
-
14
-
-
38349096680
-
-
McGarrigle E M., Myers E L., Illa O, Shaw M A., Riches S L., Aggarwal V K., Chem. Rev. 2007 107 5841
-
(2007)
Chem. Rev.
, vol.107
, pp. 5841
-
-
McGarrigle, E.M.1
Myers, E.L.2
Illa, O.3
Shaw, M.A.4
Riches, S.L.5
Aggarwal, V.K.6
-
26
-
-
0035801624
-
-
For reviews on desymmetrization of cyclic anhydrides, see:
-
For reviews on desymmetrization of cyclic anhydrides, see:, Spivey A C., Andrews B I., Angew. Chem. Int. Ed. 2001 40 3131
-
(2001)
Angew. Chem. Int. Ed.
, vol.40
, pp. 3131
-
-
Spivey, A.C.1
Andrews, B.I.2
-
29
-
-
40149101110
-
-
Rho H S., Oh S H., Lee J W., Lee J Y., Chin J, Song C E., Chem. Commun. 2008 1208
-
(2008)
Chem. Commun.
, pp. 1208
-
-
Rho, H.S.1
Oh, S.H.2
Lee, J.W.3
Lee, J.Y.4
Chin, J.5
Song, C.E.6
-
30
-
-
54749152753
-
-
Oh S H., Rho H S., Lee J W., Lee J E., Youk S H., Chin J, Song C E., Angew. Chem. Int. Ed. 2008 47 7872
-
(2008)
Angew. Chem. Int. Ed.
, vol.47
, pp. 7872
-
-
Oh, S.H.1
Rho, H.S.2
Lee, J.W.3
Lee, J.E.4
Youk, S.H.5
Chin, J.6
Song, C.E.7
-
33
-
-
24944473938
-
-
Honjo T, Sano S, Shiro M, Nagao Y, Angew. Chem. Int. Ed. 2005 44 5838
-
(2005)
Angew. Chem. Int. Ed.
, vol.44
, pp. 5838
-
-
Honjo, T.1
Sano, S.2
Shiro, M.3
Nagao, Y.4
-
39
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note
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General Experimental Procedure for Chiral Sulfonamide 1 Catalyzed Alcoholysis of Cyclic Dicarboxylic Anhydrides To a solution of 3-phenylglutaric anhydride (2a, 190 mg, 1.0 mmol) and chiral sulfonamide 1 (25.8 mg, 0.05 mmol) in Et2O (10 mL) was added BnOH (125 mL, 1.2 mmol) at r.t. After stirring at r.t. for 20 h, the reaction mixture was treated with 10% HCl followed by extraction with CHCl3. The extract was dried over anhyd MgSO4, filtered, and concentrated in vacuo. To a solution of the residue in benzene MeOH (7:2, 9 mL) was added a solution of TMSCHN2 (2.0 M in Et2O, 1 mL, 2.0 mmol). After being stirred at r.t. for 15 min, the reaction mixture was evaporated in vacuo. The oily residue was purified by silica gel column chromatography [EtOAc n-hexane (1:4)] to afford methyl ester (S)-4a (286 mg, 92% yield, 87% ee) as a colorless oil. The ee (%) of (S)-4a was determined on a Chiralpak AD-H column [Daicel, eluent: n-hexane 2-PrOH (15:1), flow rate: 1 mL/min, detection: 254 nm]. The retention times were 12.5 min [minor isomer, (R)-4a] and 13.8 min [major isomer, (S)-4a], respectively. The absolute configuration of (S)-4a was explicitly determined by its chemical conversion to thioester (S)-5 (Scheme 1).7 (Formula).
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For details see Supporting Information.
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For details see Supporting Information
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