M.-C. Wang et al. / Tetrahedron 64 (2008) 2559e2564
2563
549 cmꢁ1. HRMS (ESI) calcd for C14H13ClO: 215.0628
(MþꢁOH), found: 215.0636. Enantiomeric excess: 96.5%,
Chiralcel OD, 216 nm, i-PrOH/hexane¼2/98, 0.5 mL/min,
tR¼54.8 min, tS¼60.8 min.
C15H16O: 235.1099 (MþþNa), found: 235.1095. Enantiomeric
excess: 97.0%, Chiralcel OD, 216 nm, i-PrOH/hexane¼1/100,
0.5 mL/min, tR¼37.7 min, tS¼43.6 min.
4.3.9. (R)-(2-Methylphenyl)-(40-methoxyphenyl)methanol
(entry 9, Table 2)
4.3.5. (R)-(4-Chlorophenyl)-(40-methoxyphenyl)methanol
(entry 5, Table 2)
1H NMR (400 MHz, CDCl3): d 2.19 (s, 3H, CH3), 3.76 (s,
3H, OCH3), 5.92 (s, 1H, CH), 6.82e6.88 (m, 2H, ArH), 7.18e
7.25 (m, 5H, ArH), 7.54e7.55 (m, 1H, ArH). 13C NMR
(100 MHz, CDCl3): d 19.4 (CH3), 55.3 (OCH3), 72.9 (ArCH-
OHAr0), 113.9 (2CH), 126.0 (1CH), 127.2 (1CH), 127.3
(1CH), 128.5 (2CH), 130.5 (1CH), 135.1 (C), 136.8 (C), 141.7
(C), 159.0 (C). IR (KBr pellets): 3392, 3022, 2953, 2835,
1610, 1584, 1461, 1302, 1249, 1172, 1032, 861, 829, 777,
747, 646, 626, 580 cmꢁ1. HRMS (ESI) calcd for C15H16O2:
251.1048 (MþþNa), found: 251.1053. Enantiomeric excess:
83.1%, Chiralcel OD: i-PrOH/hexane¼1/100, 0.5 mL/min,
tR¼135.9 min, tS¼144.8 min.
1H NMR (400 MHz, CDCl3): d 3.78 (s, 3H, OCH3), 5.76 (s,
1H, CH), 6.85e6.89 (m, 2H, ArH), 7.23e7.25 (m, 2H, ArH),
7.26e7.29 (m, 4H, ArH). 13C NMR (100 MHz, CDCl3): d 55.3
(OCH3), 75.2 (ArCHOHAr0), 114.0 (2CH), 127.8 (2CH), 127.9
(2CH), 128.5 (2CH), 133.1 (C), 135.8 (C), 142.5 (C), 159.2 (C).
IR (KBr pellets): 3374, 2958, 2831, 1609, 1511, 1487, 1461,
1403, 1249, 1172, 1089, 1032, 857, 805, 769, 554 cmꢁ1. HRMS
(ESI) calcd for C14H13ClO2: 231.0577 (MþꢁOH), found:
231.0585. Enantiomeric excess: 93.2%, Chiralcel OD,
216 nm, i-PrOH/hexane¼2/100, 0.5 mL/min, tR¼96.0 min,
tS¼88.1 min.
4.3.6. (S)-(4-Chlorophenyl)-(40-methoxyphenyl)methanol
(entry 6, Table 2)
4.3.10. (S)-(2-Methylphenyl)-(40-methoxyphenyl)methanol
(entry 10, Table 2)
1H NMR (400 MHz, CDCl3): d 2.28 (br, 1H, OH), 3.78 (s,
3H, OCH3), 5.75 (s, 1H, CH), 6.84e6.87 (m, 2H, ArH), 7.22e
7.25 (m, 2H, ArH), 7.29 (s, 4H, ArH). 13C NMR (100 MHz,
CDCl3): d 55.3 (OCH3), 75.2 (ArCHOHAr0), 114.0 (2CH),
127.8 (2CH), 127.9 (2CH), 128.5 (2CH), 133.1 (C), 135.8
(C), 142.4 (C), 159.2 (C). IR (KBr pellets): 3374, 2958,
2831, 1609, 1511, 1487, 1461, 1403, 1249, 1172, 1089, 1032,
857, 805, 769, 554 cmꢁ1. HRMS (ESI) calcd for C14H13ClO2:
231.0577 (MþꢁOH), found: 231.0585. Enantiomeric excess:
96.3%, Chiralcel OD, 216 nm, i-PrOH/hexane¼2/100,
0.5 mL/min, tR¼94.7 min, tS¼86.3 min.
1H NMR (400 MHz, CDCl3): d 2.11 (br, 1H, OH), 2.20 (s,
3H, CH3), 3.77 (s, 3H, OCH3), 5.94 (s, 1H, CH), 6.83e6.85
(m, 2H, ArH), 7.11e7.24 (m, 5H, ArH), 7.55e7.57 (m, 1H,
ArH). 13C NMR (100 MHz, CDCl3): d 19.3 (CH3), 55.3
(OCH3), 73.0 (ArCHOHAr0), 113.9 (2CH), 125.9 (1CH),
126.1 (1CH), 127.4 (1CH), 128.5 (2CH), 130.5 (1CH), 135.1
(C), 135.2 (C), 141.6 (C), 159.1 (C). IR (KBr pellets): 3392,
3022, 2953, 2835, 1610, 1584, 1461, 1302, 1249, 1172, 1032,
861, 829, 777, 747, 646, 626, 580 cmꢁ1. HRMS (ESI) calcd
for C15H16O2: 251.1048 (MþþNa), found: 251.1053. Enantio-
meric excess: 97.5%, Chiralcel OD, 216 nm, i-PrOH/
hexane¼1/100, 0.5 mL/min, tR¼136.5 min, tS¼144.0 min.
4.3.7. (R)-(2-Methylphenyl)-(40-methylphenyl)methanol
(entry 7, Table 2)
1H NMR (400 MHz, CDCl3): d 2.22 (s, 3H, CH3), 2.32 (s,
3H, CH3), 5.94 (s, 1H, CH), 7.10e7.15 (m, 3H, ArH), 7.16e
7.23 (m, 5H, ArH), 7.51e7.53 (m, 1H, ArH). 13C NMR
(100 MHz, CDCl3): d 19.4 (CH3), 21.1 (CH3), 73.2 (ArCH-
OHAr0), 126.0 (2CH), 127.1 (3CH), 129.2 (3CH), 135.3 (C),
137.3 (C), 140.0 (C), 141.6 (C). IR (KBr pellets): 3369, 3022,
2920, 1511, 1486, 1459, 1380, 1310, 1174, 1111, 1017, 862,
815, 777, 745, 631, 573 cmꢁ1. HRMS (ESI) calcd for
C15H16O: 235.1099 (MþþNa), found: 235.1095. Enantiomeric
excess: 86.6%, Chiralcel OD, 216 nm, i-PrOH/hexane¼1/100,
0.5 mL/min, tR¼37.9 min, tS¼43.2 min.
Acknowledgements
We are grateful to the National Natural Sciences Founda-
tion of China (NNSFC: 20672102), the Ministry of Education
of China, and The Innovation Fund for Outstanding Scholar of
Henan Province (074200510005).
Supplementary data
Supplementary data associated with this article can be
4.3.8. (S)-(2-Methylphenyl)-(40-methylphenyl)methanol
(entry 8, Table 2)
References and notes
1H NMR (400 MHz, CDCl3): d 2.22 (s, 3H, CH3), 2.32 (s,
3H, CH3), 5.95 (s, 1H, CH), 7.11e7.13 (m, 3H, ArH), 7.16e
7.24 (m, 5H, ArH), 7.51e7.53 (m, 1H, ArH). 13C NMR
(100 MHz, CDCl3): d 19.4 (CH3), 21.1 (CH3), 73.2 (ArCH-
OHAr0), 126.1 (2CH), 127.1 (3CH), 129.2 (3CH), 135.3 (C),
137.3 (C), 140.0 (C), 141.6 (C). IR (KBr pellets): 3369, 3022,
2920, 1511, 1486, 1459, 1380, 1310, 1174, 1111, 1017, 862,
815, 777, 745, 631, 573 cmꢁ1. HRMS (ESI) calcd for
1. For selected active pharmaceutical ingredients, see: (a) Meguro, K.;
Aizawa, M.; Sohda, T.; Kawarnatsu, Y.; Nagaoka, A. Chem. Pharm. Bull.
1985, 33, 3787e3797; (b) Toda, F.; Tanaka, K.; Roshiro, K. Tetrahedron:
Asymmetry 1991, 2, 873e874; (c) Stanchev, S.; Rakovska, R.; Berova, N.;
Snatzke, G. Tetrahedron: Asymmetry 1995, 6, 138e198; (d) Casy, A. F.;
Drake, A. F.; Ganellin, C. R.; Merce, A. D.; Upton, C. Chirality 1992,
4, 356e366; (e) Torrens, A.; Castrillo, J. A.; Claparols, A.; Redondo, J.
Synlett 1999, 765e767; (f) Shafi’ee, A.; Hite, G. J. Med. Chem. 1969, 12,
266e270.