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dC (Me4Si) 160.2, 138.4, 134.0, 128.8, 127.6, 127.1, 126.4, 115.3 126.4, 123.8 (Ph), 80.1, 79.2 (CH). Anal. calcd for C14H13BrO2: C,
(Ph), 79.8, 78.2 (CH). Anal. calcd for C14H13FO2: C, 72.40; H, 57.36; H, 4.47; O, 10.92. Found: C, 57.31; H, 4.42; O, 10.82%.
5.64; O, 13.78. Found: C, 72.34; H, 5.57; O, 13.79%. Mass (MS): Mass (MS): m/z 293.0 [M + H]+.
m/z 233.1 [M + H]+. Daicel Chiralcel OJ-H column: (S,S)-6a2, tR ¼
6c3. 93.2%, white solid. [a]2D5 ¼ ꢁ65.8 (c 1.02, CDCl3). dH
25.36 min (major); (R,R)-6a2, tR ¼ 37.85 min; (R,S or S,R)-7a2, (300 MHz, CDCl3, Me4Si) 7.34 (d, J ¼ 8.4 Hz, 2H, Ar-H), 7.25 (d,
tR ¼ 31.70, 33.55 min.
J ¼ 3.2 Hz, 2H, Ar-H), 7.12–7.07 (m, 2H, Ar-H), 6.97 (d, J ¼ 8.4
6a3. 91.8%, white solid. dH (300 MHz, CDCl3, Me4Si) 7.26– Hz, 2H, Ar-H), [4.82 (s), 4.65 (q, J ¼ 7.5 Hz)] (2H, CHOH), 2.91 (s,
7.22 (m, 3H, Ar-H), 7.12–7.02 (m, 4H, Ar-H), 6.89 (t, J ¼ 8.7 Hz, 2H, OH). dC (Me4Si) 138.9, 137.8, 132.2, 129.0, 127.6, 127.1,
2H, Ar-H), [4.83–4.79 (m), 4.69–4.59 (m)] (2H, CHOH), 2.70 (s, 126.5, 122.0 (Ph), 80.1, 80.0 (CH3). Anal. calcd for C14H13BrO2:
2H, OH). dC (Me4Si) 162.6, 143.1, 138.3, 130.6, 129.0, 127.6, C, 57.36; H, 4.47; O, 10.92. Found: C, 57.31; H, 4.43; O, 10.86%.
127.0, 122.8, 114.4, 114.0 (Ph), 79.6, 77.8 (CH). Anal. calcd for Mass (MS): m/z 293.0 [M + H]+. Phenomenex Lux 5u Amylose-2
C
14H13FO2: C, 72.40; H, 5.64; O, 13.78. Found: C, 72.39; H, 5.63; chiral column: (S,S)-6c3, tR ¼ 43.17 min (major); (R,R)-6c3, tR ¼
O, 13.76%. Mass (MS): m/z 233.1 [M + H]+. Phenomenex Lux 5u 23.23 min; (R,S and S,R)-7c3, tR ¼ 35.72, 40.22 min.
Amylose-2 chiral column: (S,S)-6a3, tR ¼ 34.04 min (major);
6d1 + 7d1. 22.7%, white solid. dH (300 MHz, CDCl3, Me4Si)
(R,R)-6a3, tR ¼ 31.65 min; (R,S or S,R)-7a3, tR ¼ 20.96, 26.94 min. 8.12–8.04 (m, 1H, Ar-H), 7.64–7.55 (m, 1H, Ar-H), 7.50–7.45 (m,
6b1 + 7b1. 22.6%, white solid. dH (300 MHz, CDCl3, Me4Si) 1H, Ar-H), 7.36–7.28 (m, 1H, Ar-H), 7.26–7.19 (m, 2H, Ar-H), 7.15–
7.62 (d, J ¼ 6.5 Hz, 1H, Ar-H), 7.33–7.27 (m, 4H, Ar-H), 7.25–7.18 7.09 (m, 2H, Ar-H), 6.95 (d, J ¼ 7.5 Hz, 1H, Ar-H), [5.13 (d, J ¼ 5.9
(m, 2H, Ar-H), 7.15–7.11 (m, 2H, Ar-H), [5.48 (d, J ¼ 4.7 Hz), 5.26 Hz), 4.93 (d, J ¼ 7.4 Hz), 4.86 (d, J ¼ 5.9 Hz), 4.76 (d, J ¼ 7.4 Hz)]
(d, J ¼ 4.5 Hz), 5.05 (d, J ¼ 4.7 Hz), 4.95 (d, J ¼ 4.5 Hz)] (2H, (2H, CHOH), 3.57 (s, 2H, OH), [2.65 (s), 1.75 (s)] (3H, CH3). Anal.
CHOH), 2.66 (s, 2H, OH). Anal. calcd for C14H13ClO2: C, 67.61; calcd for C15H16O2: C, 78.92; H, 7.06; O, 14.02. Found: C, 78.84; H,
H, 5.27; O, 12.87. Found: C, 67.59; H, 5.23; O, 12.79%. Mass 6.95; O, 13.96%. Mass (MS): m/z 229.1 [M + H]+. Daicel Chiralcel
(MS): m/z 249.1 [M + H]+. Phenomenex Lux 5u Amylose-2 chiral OJ-H column: (S,S)-6d1, tR ¼ 20.94 min (major); (R,R)-6d1, tR
¼
column: (S,S)-6b1, tR ¼ 34.62 min (major); (R,R)-6b1, tR
27.05 min; (R,S or S,R)-7b1, tR ¼ 23.39, 24.99 min.
¼
25.56 min; (R,S and S,R)-7d1, tR ¼ 33.03 min.
6d2. 78.7%, white solid. dH (300 MHz, CDCl3, Me4Si) 7.24 (d,
6b2. 95.9%, white solid. dH (300 MHz, CDCl3, Me4Si) 7.33– J ¼ 2.2 Hz, 3H, Ar-H), 7.16–7.09 (m, 3H, Ar-H), 7.04 (d, J ¼
7.27 (m, 1H, Ar-H), 7.26–7.22 (m, 3H, Ar-H), 7.19 (s, 1H, Ar-H), 7.6 Hz, 1H, Ar-H), 6.99 (s, 1H, Ar-H), 6.90 (d, J ¼ 7.3 Hz, 1H, Ar-
7.14–7.10 (m, 3H, Ar-H), 6.90 (d, J ¼ 7.5 Hz, 1H, Ar-H), [4.84–4.79 H), [4.78 (q, J ¼ 6.4 Hz), 4.70 (q, J ¼ 7.0 Hz)] (2H, CHOH), [2.32
(m), 4.74–4.60 (m)] (2H, CHOH), 2.87 (s, 2H, OH). dC (Me4Si) (s), 2.28 (s)] (3H, CH3). dC (Me4Si) 140.8, 139.6, 138.0, 129.5,
142.8, 138.8, 134.1, 132.3, 128.6, 127.9, 127.4, 127.1, 125.7, 124.8 129.0, 128.8, 127.7, 127.2, 126.8, 124.0 (Ph), 80.3, 79.8 (CH), 21.6
(Ph), 80.0, 79.4 (CH). Anal. calcd for C14H13ClO2: C, 67.61; H, (CH3). Anal. calcd for C15H16O2: C, 78.92; H, 7.06; O, 14.02.
5.27; O, 12.87. Found: C, 67.55; H, 5.20; O, 12.72%. Mass (MS): Found: C, 78.84; H, 6.97; O, 13.92%. Mass (MS): m/z 229.1 [M +
m/z 249.1 [M + H]+.
H]+. Daicel Chiralcel OJ-H column: (S,S)-6d2, tR ¼ 28.07 min
6b3. 97.1%, white solid. [a]2D5 ¼ ꢁ63.0 (c 0.92, CDCl3). dH (major); (R,R)-6d2, tR ¼ 25.56 min; (R,S and S,R)-7d2, tR ¼ 30.93,
(300 MHz, CDCl3, Me4Si) 7.26–7.24 (m, 3H, Ar-H), 7.21 (s, 1H, 33.20 min.
Ar-H), 7.18 (s, 1H, Ar-H), 7.17–7.09 (m, 2H, Ar-H), 7.03 (d, J ¼
6d3. 80.6%, white solid. dH (300 MHz, CDCl3, Me4Si) 7.22–
8.4 Hz, 2H, Ar-H), [4.83 (s), 4.66 (dd, J ¼ 18.9, 7.5 Hz)] (2H, 7.20 (m, 3H, Ar-H), 7.12–7.10 (m, 2H, Ar-H), 7.04–6.98 (m, 4H,
CHOH), 2.34 (s, 2H, OH). dC (Me4Si) 138.9, 137.1, 133.5, 129.7, Ar-H), [4.68 (q, J ¼ 6.2 Hz), 4.65 (q, J ¼ 7.4 Hz)] (2H, CHOH), 3.31
129.0, 128.4, 127.1, 126.4 (Ph), 80.0, 79.7 (CH). Anal. calcd for (s, 2H, OH), [2.40 (s), 2.29 (s)] (3H, CH3). dC (Me4Si) 138.0, 137.1,
C
14H13ClO2: C, 67.61; H, 5.27; O, 12.87. Found: C, 67.55; H, 134.8, 129.8, 128.6, 128.0, 127.2, 125.5 (Ph), 80.2, 80.0 (CH), 21.3
5.20; O, 12.72%. Mass (MS): m/z 249.1 [M + H]+. Phenomenex (CH3). Anal. calcd for C15H16O2: C, 78.92; H, 7.06; O, 14.02.
Lux 5u Amylose-2 chiral column: (S,S)-6b3, tR ¼ 40.39 min Found: C, 78.80; H, 7.93; O, 13.94%. Mass (MS): m/z 229.1 [M +
(major); (R,R)-6b3, tR ¼ 22.30 min; (R,S or S,R)-7b1, tR ¼ 35.31, H]+. Phenomenex Lux 5u Amylose-2 chiral column: (S,S)-6d3, tR
38.89 min.
¼ 54.11 min (major); (R,R)-6d3, tR ¼ 51.10 min; (R,S and S,R)-
6c1. 55.4%, white solid. [a]2D5 ¼ ꢁ69.3 (c 0.84, CDCl3). dH (300 7d3, tR ¼ 28.84, 44.54 min.
MHz, CDCl3, Me4Si) 7.58–7.47 (m, 6H, Ar-H), 7.12–7.06 (m, 3H,
6e1 + 7e1. 31.2%, white solid. dH (300 MHz, CDCl3, Me4Si)
Ar-H), [4.82 (s), 4.69 (s)] (2H, CHOH), 3.04 (s, 2H, OH). dC (Me4Si) 7.27 (s, 1H, Ar-H), 7.25–7.24 (m, 1H, Ar-H), 7.22–7.16 (m, 3H, Ar-
144.6, 138.4, 133.4, 130.2, 128.9, 127.9, 127.7, 127.1, 126.5, 120.3 H), 7.15–7.12 (m, 1H, Ar-H), 6.92–6.82 (m, 3H, Ar-H), [5.17 (d, J ¼
(Ph), 79.8, 76.0 (CH). Anal. calcd for C14H13BrO2: C, 57.36; H, 5.5 Hz), 4.94 (d, J ¼ 5.5 Hz), 4.86 (q, J ¼ 6.6 Hz)] (2H, CHOH),
4.47; O, 10.92. Found: C, 57.35; H, 4.40; O, 10.87%. Mass (MS): [3.76 (s), 3.71 (s)] (3H, OCH3), 2.69 (s, 2H, OH). Anal. calcd for
m/z 293.0 [M + H]+. Phenomenex Lux 5u Amylose-2 chiral C15H16O3: C, 73.75; H, 6.60; O, 19.65. Found: C, 73.69; H, 6.53;
column: (S,S)-6c1, tR ¼ 27.80 min (major); (R,R)-6c1, tR
¼
O, 19.34%. Mass (MS): m/z 245.1 [M + H]+. Phenomenex Lux 5u
Amylose-2 chiral column: (S,S)-6e1, tR ¼ 68.05 min; (R,R)-6e1,
31.90 min; (R,S and S,R)-7c1, tR ¼ 39.18 min.
6c2. 97.6%, white solid. dH (300 MHz, CDCl3, Me4Si) 7.36 (d, tR ¼ 46.31 min; (R,S and S,R)-7e1, tR ¼ 52.27, 60.47 min.
J ¼ 6.4 Hz, 2H, Ar-H), 7.30–7.27 (m, 1H, Ar-H), 7.25–7.22 (m, 2H,
6e2. 93.5%, white solid. [a]2D5 ¼ ꢁ113.6 (c 1.10, CDCl3). dH (300
Ar-H), 7.13–7.04 (m, 3H, Ar-H), 6.94 (d, J ¼ 7.7 Hz, 1H, Ar-H), MHz, CDCl3, Me4Si) 7.25–7.21 (m, 3H, Ar-H), 7.12 (t, J ¼ 7.6 Hz,
[4.81 (m), 4.71–4.62 (m)] (2H, CHOH), 2.37 (s, 2H, OH). dC 3H, Ar-H), 6.75 (dd, J ¼ 8.2, 1.9 Hz, 1H, Ar-H), 6.67 (d, J ¼ 9.2 Hz,
(Me4Si) 143.2, 138.6, 132.2, 130.8, 129.8, 129.0, 127.9, 127.3, 2H, Ar-H), [4.78 (s), 4.65 (s)] (2H, CHOH), 3.68 (s, 3H, OCH3), 2.88
6422 | RSC Adv., 2014, 4, 6417–6423
This journal is © The Royal Society of Chemistry 2014