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from the minor diastereomer by recrystallization (CH2Cl2/EtOH) to
1-[(R)-{2-[(S)-2-Methoxy-1-phenylethoxy]phenyl}(4-methoxy-
afford 10d as a white solid. [α]1D9 = –273.2 (c = 0.91, CHCl3). M.p. phenyl)methyl]naphthalen-2-ol (10h): The major diastereomer
140–141 °C. IR (KBr): ν = 3440, 1620, 1599, 1483, 1452, 1242, 820, was separated from the minor diastereomer by recrystallization
˜
764, 746, 700 cm–1
.
1H NMR (CDCl3): δ = 8.13 (d, J = 9.0 Hz, 1 H),
(EtOH) to afford 10h as a pale-brownish solid. [α]2D2 = –191.6 (c =
7.79 (d, J = 8.0 Hz, 1 H), 7.73 (d, J = 9.0 Hz, 1 H), 7.47–7.39 (m, 1 H),
7.32 (dd, J = 8.0, 7.0 Hz, 1 H), 7.25–7.19 (m, 3 H), 7.16 (d, J = 8.5 Hz,
2 H), 7.14–7.04 (m, 7 H), 6.85–6.74 (m, 3 H), 5.57 (br. s, 1 H), 5.34
(dd, J = 8.0, 4.0 Hz, 1 H), 3.47 (dd, J = 10.5, 8.0 Hz, 1 H), 3.38 (dd,
J = 10.5, 4.0 Hz, 1 H), 3.27 (s, 3 H), 2.37 (s, 3 H) ppm. 13C NMR
(CDCl3): δ = 155.5, 153.2, 138.7, 138.4, 136.8, 133.7, 130.1, 129.9,
129.8, 129.5, 129.2, 128.6, 128.48, 128.45, 128.2, 127.9, 126.6, 126.2,
123.3, 123.0, 121.2, 120.2, 119.8, 113.1, 79.3, 76.8, 59.2, 42.6,
21.9 ppm. HRMS: calcd. for C33H30O3 [M + Na]+ 497.2087; found
497.2077.
1.09, CHCl3). M.p. 70–71 °C. IR (KBr): ν = 3474, 1601, 1508, 1485,
˜
1452, 1242, 816, 750, 700 cm–1
.
1H NMR (CDCl3): δ = 8.12 (d, J =
8.5 Hz, 1 H), 7.78 (d, J = 8.0 Hz, 1 H), 7.73 (d, J = 8.5 Hz, 1 H), 7.46–
7.39 (m 1 H), 7.35–7.29 (m, 1 H), 7.25–7.19 (m, 3 H), 7.13 (d, J =
8.5 Hz, 2 H), 7.11–7.05 (m, 5 H), 6.89 (d, J = 9.0 Hz, 2 H), 6.85–6.75
(m, 3 H), 5.60 (br. s, 1 H), 5.33 (dd, J = 7.5, 4.0 Hz, 1 H), 3.43 (dd, J =
10.5, 7.5 Hz, 1 H), 3.37 (dd, J = 10.5, 4.0 Hz, 1 H), 3.82 (s, 3 H), 3.26
(s, 3 H) ppm. 13C NMR (CDCl3): δ = 158.7, 155.5, 153.3, 138.4, 133.7,
133.6, 130.4, 129.8, 129.8, 129.6, 129.2, 128.50, 128.47, 128.2, 128.0,
126.6, 126.2, 123.3, 123.0, 121.2, 120.1, 119.8, 114.5, 113.1, 79.3, 76.8,
59.1, 55.3, 42.2 ppm. HRMS: calcd. for C33H30O4 [M + Na]+ 513.2036;
found 513.2040.
1-[(R)-(3,4-Dimethylphenyl){2-[(S)-2-methoxy-1-phenylethoxy]-
phenyl}methyl]naphthalen-2-ol (10e): The major diastereomer
was separated from the minor diastereomer by recrystallization
(EtOH) to afford 10e as a pale-yellow solid. [α]2D2 = –206.3 (c = 1.12,
1-[(R)-(2-Chlorophenyl){2-[(S)-2-methoxy-1-phenylethoxy]-
phenyl}methyl]naphthalen-2-ol (10i): The major diastereomer
CHCl3). M.p. 73–75 °C. IR (KBr): ν = 3474, 1622, 1601, 1485, 1452, was separated from the minor diastereomer by preparative thin-
˜
1238, 1202, 814, 750, 700 cm–1
.
1H NMR (CDCl3): δ = 8.13 (d, J =
layer chromatography on silica gel (hexane/CHCl3/MeOH =
8.5 Hz, 1 H), 7.78 (d, J = 8.0 Hz, 1 H), 7.73 (d, J = 9.0 Hz, 1 H), 7.44
(ddd, J = 8.5, 7.0, 1.0 Hz, 1 H), 7.32 (t, J = 7.5 Hz, 1 H), 7.26–7.17 (m,
3 H), 7.14–7.03 (m, 6 H), 6.99 (s, 1 H), 6.93 (d, J = 7.5 Hz, 1 H), 6.84–
6.74 (m, 3 H), 5.62 (br. s, 1 H), 5.35 (dd, J = 8.0, 4.0 Hz, 1 H), 3.49
(dd, J = 10.5, 8.0 Hz, 1 H), 3.40 (dd, J = 10.5, 4.0 Hz, 1 H), 3.29 (s, 3
H), 2.27 (s, 3 H), 2.20 (s, 3 H) ppm. 13C NMR (CDCl3): δ = 155.4, 153.3,
50:99:1 × 2) to afford 10i as a brownish solid. [α]2D3 = +20.0 (c =
2.29, CHCl3). M.p. 66–68 °C. IR (KBr): ν = 3483, 1622, 1599, 1485,
˜
1
1452, 1238, 1205, 1126, 1049, 814, 748, 700 cm–1. H NMR (CDCl3):
δ = 8.18 (d, J = 8.5 Hz, 1 H), 7.78 (dd, J = 8.0, 1.5 Hz, 1 H), 7.73 (d,
J = 8.5 Hz, 1 H), 7.51–7.41 (m, 2 H), 7.32 (ddd, J = 8.5, 7.0, 1.0 Hz, 1
H), 7.29–7.17 (m, 6 H), 7.16–7.03 (m, 4 H), 6.98 (s, 1 H), 6.92 (d, J =
139.1, 138.4, 137.5, 135.5, 133.7, 130.4, 130.1, 129.9, 129.9, 129.5, 7.0 Hz, 1 H), 6.84 (dt, J = 1.0, 7.5 Hz, 1 H), 6.78 (d, J = 8.0 Hz, 1 H),
129.2, 128.5, 128.4, 128.1, 127.9, 126.7, 126.2, 126.0, 123.2, 123.0, 5.57 (br. s, 1 H), 5.26 (d, J = 7.0, 4.0 Hz, 1 H), 3.20 (br. s, 2 H), 2.92
121.1, 120.3, 119.9, 113.0, 79.2, 76.8, 59.2, 42.5, 19.9, 19.4 ppm.
(br. s, 3 H) ppm. 13C NMR (CDCl3): δ = 155.7, 153.3, 139.5, 138.2,
134.7, 133.6, 130.7, 130.2, 129.7, 129.5, 129.3, 129.0, 128.8, 128.6,
128.5, 128.4, 127.9, 127.2, 126.7, 126.2, 123.04, 122.96, 121.2, 119.6,
118.4, 113.4, 79.3, 76.5, 58.9, 41.9 ppm. HRMS: calcd. for C32H27ClO3
[M + Na]+ 517.1541; found 517.1543.
HRMS: calcd. for C34H32O3 [M + H]+ 511.2244; found 511.2235.
1-[(R)-{2-[(S)-2-Methoxy-1-phenylethoxy]phenyl}(2-methoxy-
phenyl)methyl]naphthalen-2-ol (10f): The major diastereomer
was separated from the minor diastereomer by recrystallization
(EtOH) to afford 10f as a pale-yellow solid. [α]2D4 = –7.96 (c = 0.79,
1-[(R)-(3-Chlorophenyl){2-[(S)-2-methoxy-1-phenylethoxy]-
CHCl3). M.p. 75–76 °C. IR (KBr): ν = 3476, 1599, 1487, 1452, 1240, phenyl}methyl]naphthalen-2-ol (10j): The major diastereomer
˜
816, 752, 700 cm–1
.
1H NMR (CDCl3): δ = 8.08 (d, J = 9.0 Hz, 1 H),
was separated from the minor diastereomer by recrystallization
7.76 (d, J = 8.0 Hz, 1 H), 7.69 (d, J = 8.5 Hz, 1 H), 7.44–7.38 (m, 1 H),
(EtOH) to afford 10j as a white solid. [α]2D5 = –280.7 (c = 0.56, CHCl3).
7.34–7.27 (m, 2 H), 7.24–7.18 (m, 3 H), 7.14–7.01 (m, 5 H), 7.01–6.94 M.p. 80–81 °C. IR (KBr): ν = 3489, 1593, 1485, 1452, 1238, 814, 750,
˜
(m, 3 H), 6.91 (t, J = 7.5 Hz, 1 H), 6.80 (t, J = 7.0 Hz, 1 H), 6.76 (d, 700 cm–1 1H NMR (CDCl3): δ = 8.05 (d, J = 8.5 Hz, 1 H), 7.79 (dd,
.
J = 8.5 Hz,1 H), 5.77 (br. s, 1 H), 5.27 (dd, J = 4.5, 4.0 Hz, 1 H), 3.70
J = 8.0, 1.0 Hz, 1 H), 7.75 (d, J = 9.0 Hz, 1 H), 7.43 (ddd, J = 8.5, 7.0,
1.5 Hz, 1 H), 7.33 (ddd, J = 8.5, 7.0, 1.0 Hz, 1 H), 7.30–7.22 (m, 5 H),
(s, 3 H), 3.20 (br. s, 2 H), 2.98 (br. s, 3 H) ppm. 13C NMR (CDCl3): δ =
157.4, 155.5, 153.3, 138.4, 133.7, 130.7, 129.8, 129.8, 129.6, 128.9, 7.21–7.17 (m, 1 H), 7.14–7.05 (m, 6 H), 6.83 (dt, J = 1.0, 8.0 Hz, 1 H),
128.7, 128.42, 128.37, 128.25, 127.8, 126.4, 126.3, 126.3, 123.3, 122.8, 6.78 (d, J = 8.0 Hz, 1 H), 6.76 (s, 1 H), 5.49 (br. s, 1 H), 5.30 (dd, J =
121.0, 121.0, 119.6, 119.3, 113.1, 111.1, 79.0, 76.4, 59.0, 55.7,
38.1 ppm. HRMS: calcd. for C33H30O4 [M + Na]+ 513.2036; found
513.2030.
8.0, 4.0 Hz, 1 H), 3.39 (dd, J = 10.5, 8.0 Hz, 1 H), 3.31 (dd, J = 10.5,
4.0 Hz, 1 H), 3.19 (s, 3 H) ppm. 13C NMR (CDCl3): δ = 155.6, 152.9,
144.4, 138.1, 134.9, 133.5, 130.1, 129.8, 129.7, 129.5, 129.3, 128.8,
128.6, 128.1, 127.1, 126.9, 126.7, 126.2, 123.3, 123.1, 121.4, 119.8,
119.5, 79.5, 76.6, 59.0, 42.8 ppm. HRMS: calcd. for C32H27ClO3 [M +
Na]+ 517.1541; found 517.1531.
1-[(R)-{2-[(S)-2-Methoxy-1-phenylethoxy]phenyl}(3-methoxy-
phenyl)methyl]naphthalen-2-ol (10g): The major diastereomer
was separated from the minor diastereomer by recrystallization
(EtOH) to afford 10g as a pale-yellow solid. [α]2D0 = –192.9 (c = 1.18, 1-[(R)-(4-Chlorophenyl){2-[(S)-2-methoxy-1-phenylethoxy]-
CHCl3). M.p. 68–69 °C. IR (KBr): ν = 3481, 1599, 1582, 1485, 1452, phenyl}methyl]naphthalen-2-ol (10k): The major diastereomer
˜
1
1238, 820, 750, 700 cm–1. H NMR (CDCl3): δ = 8.12 (d, J = 8.5 Hz,
1 H), 7.79 (d, J = 8.0 Hz, 1 H), 7.74 (d, J = 9.0 Hz, 1 H), 7.48–7.40 (m,
1 H), 7.33 (dd, J = 7.5, 7.0 Hz, 1 H), 7.30–7.19 (m, 4 H), 7.14–7.04 (m,
5 H), 6.86 (dd, J = 8.0, 2.0 Hz, 1 H), 6.84–6.74 (m, 5 H), 5.17 (br. s, 1
H), 5.35 (dd, J = 8.0, 4.0 Hz, 1 H), 3.49 (dd, J = 10.5, 8.0 Hz, 1 H),
was separated from the minor diastereomer by recrystallization
(EtOH) to afford 10k as a pale-yellow solid. [α]1D9 = –145.2 (c = 1.16,
CHCl3). M.p. 75–76 °C. IR (KBr): ν = 3503, 1622, 1599, 1487, 1452,
˜
1
1238, 814, 750, 700 cm–1. H NMR (CDCl3): δ = 8.06 (d, J = 9.0 Hz,
1 H), 7.80 (d, J = 8.5 Hz, 1 H), 7.75 (d, J = 8.5 Hz, 1 H), 7.43 (dt, J =
3.39 (dd, J = 10.5, 4.0 Hz, 1 H), 3.71 (s, 3 H), 3.29 (s, 3 H) ppm. 13C 1.5, 8.0 Hz, 1 H), 7.37–7.20 (m, 6 H), 7.19–7.05 (m, 7 H), 6.87–6.78
NMR (CDCl3): δ = 160.3, 155.4, 153.3, 143.8, 138.3, 133.7, 130.1,
(m, 2 H), 6.76 (s, 1 H), 5.53 (br. s, 1 H), 5.31 (dd, J = 7.5, 4.0 Hz, 1 H),
129.9, 129.8, 129.5, 129.3, 128.5, 128.5, 128.3, 128.0, 126.7, 126.2, 3.40 (dd, J = 10.5, 7.5 Hz, 1 H), 3.32 (dd, J = 10.5, 4.0 Hz, 1 H), 3.20
123.2, 123.0, 121.2, 120.9, 119.9, 119.8, 114.4, 113.1, 112.5, 79.3, 76.8,
59.2, 55.1, 42.9 ppm. HRMS: calcd. for C33H30O4 [M + Na]+ 513.2036;
found 513.2030.
(s, 3 H) ppm. 13C NMR (CDCl3): δ = 155.7, 153.0, 140.6, 138.2, 133.5,
132.6, 130.1, 129.8, 129.73, 129.68, 129.5, 129.0, 128.61, 128.57,
128.54, 128.1, 126.7, 126.2, 123.3, 123.1, 121.4, 119.8, 119.7, 113.4,
Eur. J. Org. Chem. 2017, 7075–7086
7082
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim