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13
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34250755191
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[12] in water, the enzyme is likely to bind the deprotonated rather than neutral forms of thiolactomycin (21) and malonyl-ACP (22). (Chemical Equation Presented).
-
[12] in water, the enzyme is likely to bind the deprotonated rather than neutral forms of thiolactomycin (21) and malonyl-ACP (22). (Chemical Equation Presented).
-
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14
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34250725170
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Dissertation in preparation, Universität Freiburg
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K. L. Dormann, Dissertation in preparation, Universität Freiburg.
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Dormann, K.L.1
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15
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34250727300
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From titrations of 5-10 μM aqueous solutions with 0.1M NaOH from a Schellbach burette using a membrane pH meter HI 8314 (HANNA instruments) and with graphical interpretation of data.
-
From titrations of 5-10 μM aqueous solutions with 0.1M NaOH from a Schellbach burette using a membrane pH meter HI 8314 (HANNA instruments) and with graphical interpretation of data.
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16
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0021205494
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C.-L. J. Wang, J. M. Salvino, Tetrahedron Lett. 1984, 25, 5243-5246 (11% yield over the five steps from methyl α-propionate).
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C.-L. J. Wang, J. M. Salvino, Tetrahedron Lett. 1984, 25, 5243-5246 (11% yield over the five steps from methyl α-propionate).
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17
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0038680325
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J. M. McFadden, G. L. Frehywot, C. A. Townsend, Org. Lett. 2002, 4, 3859-3862.
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McFadden, J.M.1
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33747888539
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K.-i. Toyama, T. Tauchi, N. Mase, H. Yoda, K. Takabe, Tetrahedron Lett. 2006, 47, 7163-7166. The authors reported the synthesis of R-(-)-thiolactomycin but meant R-(+)-thiolactomycin (personal communication between N.M. and R.B.).
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K.-i. Toyama, T. Tauchi, N. Mase, H. Yoda, K. Takabe, Tetrahedron Lett. 2006, 47, 7163-7166. The authors reported the synthesis of "R-(-)"-thiolactomycin but meant R-(+)-thiolactomycin (personal communication between N.M. and R.B.).
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21
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0035935202
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a) S. M. Sakya, M. Suarez-Contreras, J. P. Dirlam, T. N. O'Connell, S. F. Hayashi, S. L. Santoro, B. J. Kamicker, D. M. George, C.B. Ziegler, Bioorg. Med. Chem. Lett. 2001, 11, 2751-2754;
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22
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30444441272
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b) P. Kim, Y.-M. Zhang, G. Shenoy, Q.-A. Nguyen, H. I. Boshoff, U. H. Manjunatha, M. B. Goodwin, J. Lonsdale, A. C. Proce, D. J. Miller, K. Duncan, S. W. White, C. O. Rock, C. E. Barry III, C. S. Dowd, J. Med. Chem. 2006, 49, 159-171.
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Dowd, C.S.15
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23
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0141433395
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Racemic analogues of (+)-1 synthesized since 2003: a) S. J. Senior, P. A. Illarionov, S. S. Gurcha, I. B. Campbell, M. L. Schaeffer, D. E. Minnikin, G. S. Besra, Bioorg. Med. Chem. Lett. 2003, 13, 3685-3688;
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Racemic analogues of (+)-1 synthesized since 2003: a) S. J. Senior, P. A. Illarionov, S. S. Gurcha, I. B. Campbell, M. L. Schaeffer, D. E. Minnikin, G. S. Besra, Bioorg. Med. Chem. Lett. 2003, 13, 3685-3688;
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24
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34250759049
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Ref, 4b];
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b) Ref. [4b];
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25
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13944267828
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c) J. M. McFadden, S. M. Medghalchi, J. N. Thupari, M. L. Pinn, A. Vadlamudi, K. I. Miller, F. P. Kuhajda, C. A. Townsend, J. Med. Chem. 2005, 48, 946-961;
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Kuhajda, F.P.7
Townsend, C.A.8
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26
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15044344526
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d) A. Kamal, A. A. Shaik, R. Sinha, J. S. Yadav, S. K. Arora, Bioorg. Med. Chem. Lett. 2005, 15, 1927-1929;
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Kamal, A.1
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27
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33646058268
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e) P. Kim, C. E. Barry III, C. S. Dowd, Tetrahedron Lett. 2006, 47, 3447-3451.
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Kim, P.1
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28
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37049081969
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Enantiomerically pure analogues of (+)-1: a) M. S. Chambers, E. J. Thomas, D. J. Williams, J. Chem. Soc. Chem. Commun. 1987, 1228-1230;
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Enantiomerically pure analogues of (+)-1: a) M. S. Chambers, E. J. Thomas, D. J. Williams, J. Chem. Soc. Chem. Commun. 1987, 1228-1230;
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-
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29
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34250752042
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Ref, 17];
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b) Ref. [17];
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31
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34250706018
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Ref, 18];
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d) Ref. [18];
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32
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34250778085
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Ref, 15];
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e)Ref. [15];
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33
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34250776268
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Ref, 19e
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f) Ref. [19e].
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34
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34250706017
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Dissertation, Universität Freiburg
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O. Böhnke, Dissertation, Universität Freiburg, 2002.
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Böhnke, O.1
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35
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0025236519
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3; they proceeded with a 1:1 ratio of syn/anti attack: E. J. Corey, W.-G. Su, Tetrahedron Lett. 1990, 31, 2113-2116.
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3; they proceeded with a 1:1 ratio of syn/anti attack: E. J. Corey, W.-G. Su, Tetrahedron Lett. 1990, 31, 2113-2116.
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36
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49149145492
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N′ openings of vinyl epoxides: a R. M. Magid, Tetrahedron 1980, 36, 1901-1930;
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N′ openings of vinyl epoxides: a) R. M. Magid, Tetrahedron 1980, 36, 1901-1930;
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37
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33845183760
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b) J. A. Marshall, Chem. Rev. 1989, 89, 1503-1511.
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Marshall, J.A.1
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6844254916
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N′ openings of vinyl epoxides: c B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422;
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N′ openings of vinyl epoxides: c) B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422;
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40
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0001190296
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Eds, M. Beller, C. Bolm, Wiley-VCH, Weinheim
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e) A. Heumann in Transition Metals in Organic Synthesis (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 2004, pp. 307-320.
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Transition Metals in Organic Synthesis
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Heumann, A.1
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41
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0001499237
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With Pd catalysis, alkoxycarbonyl-substituted vinyl epoxides related to 4 underwent stereoselective ring openings by O nucleophiles, albeit in the SN rather than SN′ mode: B. M. Trost, J. K. Lynch, S. R. Angle, Tetrahedron Lett. 1987, 28, 375-378
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N′ mode: B. M. Trost, J. K. Lynch, S. R. Angle, Tetrahedron Lett. 1987, 28, 375-378.
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42
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0012815040
-
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IV tartrate: T. Katsuki, K. B. Sharpless, J. Am. Chem. Soc. 1980, 102, 5974-5976;
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IV tartrate: T. Katsuki, K. B. Sharpless, J. Am. Chem. Soc. 1980, 102, 5974-5976;
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43
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16044372017
-
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IV tartrate: R. M. Hanson, K. B. Sharpless, J. Org. Chem. 1986, 51, 1922-1925;
-
IV tartrate: R. M. Hanson, K. B. Sharpless, J. Org. Chem. 1986, 51, 1922-1925;
-
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44
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18844410382
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Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, K. B. Sharpless, J. Am. Chem. Soc. 1987, 109, 5765-5780.
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Gao, Y.1
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Sharpless, K.B.6
-
45
-
-
34250772104
-
-
13C NMR, and IR spectra (except 11, 12) and correct combustion analyses (except 11; low-resolution MS for 10; high-resolution MS for 12, 17-19).
-
13C NMR, and IR spectra (except 11, 12) and correct combustion analyses (except 11; low-resolution MS for 10; high-resolution MS for 12, 17-19).
-
-
-
-
46
-
-
34250722402
-
-
Aldehyde 5 is an intermediate of the industrial synthesis of vitamin A by BASF.
-
Aldehyde 5 is an intermediate of the industrial synthesis of vitamin A by BASF.
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47
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0345276518
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First SAE of an alkoxycarbonyl-substituted pentadienol: T. Takahashi, H. Watanabe, T. Kitahara, Tetrahedron Lett. 2003, 44, 9219-9222.
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First SAE of an alkoxycarbonyl-substituted pentadienol: T. Takahashi, H. Watanabe, T. Kitahara, Tetrahedron Lett. 2003, 44, 9219-9222.
-
-
-
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48
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34250755190
-
-
r(major enantiomer).
-
r(major enantiomer).
-
-
-
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49
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33845378115
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Footnote [25] in: M. Caron, K. B. Sharpless, J. Org. Chem. 1985, 50, 1557-1560.
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Footnote [25] in: M. Caron, K. B. Sharpless, J. Org. Chem. 1985, 50, 1557-1560.
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51
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0000526471
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b) K. Maruoka, S. Nagahara, T. Ooi, H. Yamamoto, Tetrahedron Lett. 1989, 30, 5607-5610;
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Maruoka, K.1
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53
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33947085066
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2AlSAc (prepared as described by E. J. Corey, D. J. Beames, J. Am. Chem. Soc. 1973, 95, 5829-5831):
-
2AlSAc (prepared as described by E. J. Corey, D. J. Beames, J. Am. Chem. Soc. 1973, 95, 5829-5831):
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54
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0027155984
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R. C. Newbold, T. L. Shih, H. Mrozik, M. H. Fisher, Tetrahedron Lett. 1993, 34, 3825-3828.
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Newbold, R.C.1
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55
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34250759572
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13: Thiopropionic acid (1.03 g, 11.4 mmol, 5.0 equiv) in CH 2Cl2 (40 mL) was added to AlMe3 (2.0M in heptane, 5.7 mL, 11 mmol, 5.0 equiv) in CH2Cl2 (40 mL) at -78°C over 25 min. The reaction mixture was allowed to warm to room temperature during 60 min and then recooled to -78°C. A solution of vinyl epoxide 4 (93% ee in this experiment; 1.0 g, 2.3 mmol) in CH 2Cl2 (40 mL) was then added over 40 min. The resulting mixture was slowly warmed to room temperature and stirred for 30 min. After the addition of NaOH (1M, 40 mL) and phase separation, the aqueous layer was extracted with CH2Cl2 (3 x 60 mL, The combined organic phases were washed with H2O (80 mL) and saturated Na/K tartrate solution (80 mL, dried over MgSO4, and concentrated under vacuum. The residue was chromatographed on silica gel eluent cyclohexane/ethyl ace
-
5SSi (528.8): C 65.87, H 7.62, S 6.06; found: C 65.70, H 7.59, S 6.09.
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56
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84985702456
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Method: P. J. Garegg, B. Samuelsson, Synthesis 1979, 469-470.
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Method, P.J.1
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57
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34250692300
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The ee values of (+)-1, (+)-17, (+)-18, and (+)-19 varied somewhat (90-95%) because their precursors were derived from different samples of vinyl epoxide 4 and its α-ethyl analogue. The enantiopurity of these epoxides depended critically on the epoxidizing temperature and was not always the same.
-
The ee values of (+)-1, (+)-17, (+)-18, and (+)-19 varied somewhat (90-95%) because their precursors were derived from different samples of vinyl epoxide 4 and its α-ethyl analogue. The enantiopurity of these epoxides depended critically on the epoxidizing temperature and was not always the same.
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0024401868
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0020680673
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