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Organic & Biomolecular Chemistry
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ARTICLE
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2.36 (s, 6H). MS(ESI): m/z=467.2 [M+Na]+. The NMR spectra were 61% Yield, white solid. H NMR (500 MHz, CDCl3) δ 7.82 (d, J = 7.4
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consistent with literature values.3c
Hz, 4H), 7.51 (t, J = 7.4 Hz, 2H), 7.45 (d, J =D8O.4I: 1H0z.1,043H9)/,C79.O3B50(2t7,3J5A=
7.8 Hz, 4H), 7.18 (d, J = 8.4 Hz, 4H), 4.61 – 4.52 (m, 2H), 3.91 – 3.84
DL-((1R,2R,3S,4S)-3,4-bis(4-methoxyphenyl)cyclobutane-1,2-
diyl)bis(phenylmethanone)
(2c).
(E)-1-(4-methoxyphenyl)-3- (m, 2H). MS(ESI): m/z=595.0 [M+Na]+. The NMR spectra were
phenylprop-2-en-1-one (0.119 g, 0.5 mmol), and t-Bu-4CzIPN (0.006 consistent with literature values.3c
g, 1 mol%) in 1,4-dioxane (5 mL) gave 2c. Eluted with hexane/ethyl
DL- ((1R,2R,3S,4S)-3,4-diphenylcyclobutane-1,2-diyl)bis((4-
acetate = 95:5 to afford the desired major isomer product. 89.3 mg. chlorophenyl)methanone) (2i). (E)-1-(4-chlorophenyl)-3-phenylprop-
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75% yield, white solid. H NMR (500 MHz, CDCl3) δ 7.84 (d, J = 7.2 2-en-1-one (0.121 g, 0.5 mmol), and t-Bu-4CzIPN (0.006 g, 1 mol%)
Hz, 4H), 7.49 (t, J = 7.4 Hz, 2H), 7.34 (t, J = 7.8 Hz, 4H), 7.26 (d, J = in 1,4-dioxane (5 mL) gave 2i. Eluted with hexane/ethyl acetate =
15.8 Hz, 4H), 6.86 (d, J = 8.7 Hz, 4H), 4.66 – 4.52 (m, 2H), 3.89 – 3.82 95:5 to afford the desired major isomer product. 73.8 mg, 61%
(m, 2H), 3.80 (s, 6H). MS(ESI): m/z=499.2 [M+Na]+. The NMR spectra yield, white solid. 1H NMR (500 MHz, CDCl3) δ 7.77 (d, 4H), 7.37 –
were consistent with literature values.3c
7.26 (m, 14H), 4.62 – 4.51 (m, 2H), 3.96 – 3.91 (m, 2H). MS(ESI):
m/z=507.1 [M+Na]+. The NMR spectra were consistent with
DL-((1R,2R,3S,4S)-3,4-bis(4-
(trifluoromethyl)phenyl)cyclobutane-1,2-diyl)bis(phenylmethanone)
DL- ((1R,2R,3S,4S)-3,4-diphenylcyclobutane-1,2-diyl)bis(p-
tolylmethanone) (2d). (E)-1-phenyl-3-(p-tolyl)prop-2-en-1-one
(0.111g, 0.5 mmol), and t-Bu-4CzIPN (0.006 g, 1 mol%) in 1,4-
dioxane (5 mL) gave 2d. Eluted with hexane/ethyl acetate = 95:5 to
afford the desired major isomer product. 76.6 mg, 69% yield, white
solid. 1H NMR (500 MHz, CDCl3) δ 7.75 (d, J = 8.3 Hz, 4H), 7.37 –
(2j).
(E)-1-phenyl-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one
(0.138 g, 0.5 mmol), and t-Bu-4CzIPN (0.006 g, 1 mol%) in 1,4-
7.29 (m, 8H), 7.27 – 7.23 (m, 2H), 7.13 (d, J = 8.0 Hz, 4H), 4.64 – 4.58 dioxane (5 mL) gave 2j. Eluted with hexane/ethyl acetate = 95:5 to
(m, 2H), 4.04 – 3.95 (m, 2H), 2.34 (s, 6H). MS(ESI): m/z=467.2
[M+Na]+. The NMR spectra were consistent with literature values.3c
DL-((1R,2R,3S,4S)-3,4-diphenylcyclobutane-1,2-diyl)bis(p-
afford the desired major isomer product. 89.7 mg, yield 65%, white
solid. 1H NMR (500 MHz, CDCl3) δ 7.82 (d, J = 7.5 Hz, 4H), 7.60 (d, J =
8.2 Hz, 4H), 7.52 (t, J = 7.4 Hz, 4H), 7.43 (d, J = 8.1 Hz, 4H), 7.35 (t, J
tolylmethanone)
(2e).
(E)-1-phenyl-3-(o-tolyl)prop-2-en-1-one = 7.8 Hz, 4H), 4.64 – 4.61 (m, 2H), 4.11 – 4.05 (m, 2H). MS(ESI):
(0.111 g, 0.5 mmol), and t-Bu-4CzIPN (0.006 g, 1 mol%) in 1,4- m/z=575.1 [M+Na]+. The NMR spectra were consistent with
dioxane (5 mL) gave 2e. Eluted with hexane/ethyl acetate = 95:5 to literature values.3c
afford the desired major isomer product. 38.9 mg, 35% yield, yellow
DL-((1R,2R,3S,4S)-3,4-di-p-tolylcyclobutane-1,2-diyl)bis(p-
solid. 1H NMR (500 MHz, CDCl3) δ 7.88 – 7.78 (m, 6H), 7.48 (t, J = 7.5 tolylmethanone) (2k). (E)-1,3-di-p-tolylprop-2-en-1-one (0.118 g, 0.5
Hz, 2H), 7.40 – 7.29 (m, 6H), 7.14 (t, J = 7.4, 1.0 Hz, 2H), 7.01 (d, J = mmol), and t-Bu-4CzIPN (0.006 g, 1 mol%) in 1,4-dioxane (5 mL)
7.5 Hz, 2H), 4.71 – 4.62 (m, 2H), 4.27 – 4.15 (m, 2H), 1.94 (s, 6H). gave 2k. Eluted with hexane/ethyl acetate = 95:5 to afford the
MS(ESI): m/z=467.2 [M+Na]+. The NMR spectra were consistent desired major isomer product. 87.3 mg, 74% yield, white solid. H
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with literature values.3c
NMR (500 MHz, CDCl3) δ 7.74 (d, J = 8.2 Hz, 4H), 7.22 (d, J = 8.0 Hz,
DL-((1R,2R,3S,4S)-3,4-bis(2-methoxyphenyl)cyclobutane-1,2-
4H), 7.16 – 7.09 (m, 8H), 4.62 – 4.51 (m, 2H), 3.96 – 3.80 (m, 2H),
diyl)bis(phenylmethanone)
(2f).
(E)-3-(2-methoxyphenyl)-1- 2.34 (d, J = 4.8 Hz, 12H). MS(ESI): m/z=495.2 [M+Na]+. The NMR
phenylprop-2-en-1-one (0.119 g, 0.5 mmol), and t-Bu-4CzIPN (0.006 spectra were consistent with literature values.3c
g, 1 mol%) in 1,4-dioxane (5 mL) gave 2f. Eluted with hexane/ethyl
DL-((1R,2R,3S,4S)-3,4-bis(4-bromophenyl)cyclobutane-1,2-
acetate = 95:5 to afford the desired major isomer product. 54.7 mg, diyl)bis(p-tolylmethanone) (2l). (E)-3-(4-bromophenyl)-1-(p-
46% Yield, white solid. 1H NMR (500 MHz, CDCl3) 1H NMR (500 MHz, tolyl)prop-2-en-1-one (0.150 g, 0.5 mmol), and t-Bu-4CzIPN (0.006
CDCl3) δ 7.93 – 7.82 (m, 4H), 7.48 (t, J = 7.4 Hz, 2H), 7.44 (d, J = 7.5, g, 1 mol%) in 1,4-dioxane (5 mL) gave 2l. Eluted with hexane/ethyl
1.3 Hz, 2H), 7.35 (t, J = 7.8 Hz, 4H), 7.22 (t, J = 10.0, 5.0 Hz, 2H), 6.97 acetate = 95:5 to afford the desired major isomer product. 93.0 mg,
(t, J = 10.9, 3.9 Hz, 2H), 6.72 (d, J = 8.0 Hz, 2H), 4.54 – 4.47 (m, 2H), 62% yield, white solid. 1H NMR (500 MHz, CDCl3) δ 7.72 (d, J = 8.2
4.43 – 4.37 (m, 2H), 3.28 (s, 6H). 13C NMR (126 MHz, CDCl3) δ Hz, 4H), 7.44 (d, J = 8.4 Hz, 4H), 7.22 – 7.11 (m, J = 17.4, 8.3 Hz, 8H),
199.54, 157.11, 136.72, 132.81, 129.81, 128.43, 128.33, 127.90, 4.62 – 4.48 (m, 2H), 3.97 – 3.69 (m, 2H), 2.35 (s, 6H). 13C NMR (126
127.62, 120.70, 109.82, 54.26, 47.65, 40.18. HRMS (ESI) calcd. for MHz, CDCl3) δ 198.23, 144.66, 140.24, 132.93, 131.86, 129.38,
[M+Na]+: C32 H28 Na O4: 499.1880. Found: 499.1857.
129.07, 128.91, 121.16, 47.28, 47.24, 21.63. HRMS (ESI) calcd. for
[M+Na]+: C32 H26 Br2 Na O2 : 623.0192. Found: 623.0169.
DL-((1R,2R,3S,4S)-3,4-di-p-tolylcyclobutane-1,2-diyl)bis((4-
DL-((1R,2R,3S,4S)-3,4-bis(3-methoxyphenyl)cyclobutane-1,2-
diyl)bis(phenylmethanone)
(2g).
(E)-3-(3-methoxyphenyl)-1-
phenylprop-2-en-1-one (0.119 g, 0.5 mmol), and t-Bu-4CzIPN chlorophenyl)methanone)
(2m).
(E)-1-(4-chlorophenyl)-3-(p-
(0.006 g, 1 mol%) in 1,4-dioxane (5 mL) gave 2g. Eluted with tolyl)prop-2-en-1-one (0.128 g, 0.5 mmol), and t-Bu-4CzIPN (0.006
hexane/ethyl acetate = 95:5 to afford the desired major isomer g, 1 mol%) in 1,4-dioxane (5 mL) gave 2m. Eluted with hexane/ethyl
product. 66.6 mg, 56% Yield, yellow solid. 1H NMR (500 MHz, CDCl3) acetate = 95:5 to afford the desired major isomer product. 79.4 mg,
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δ 7.85 (dd, J = 8.3, 1.1 Hz, 2H), 7.49 (t, J = 8.0 Hz , 2H), 7.34 (t, J = 7.8 62% Yield, white solid. H NMR (500 MHz, CDCl3) δ 7.76 (d, J = 8.5
Hz, 4H), 7.25 (t, J = 7.9 Hz, 2H), 6.94 (d, J = 7.7 Hz, 2H), 6.85 – 6.84 Hz , 4H), 7.30 (d, J = 8.5 Hz, 4H), 7.19 (d, J = 8.1 Hz, 4H), 7.13 (d, J =
(m, 2H), 6.82 – 6.78 (m, 2H), 4.65 – 4.58 (m, 2H), 4.00 – 3.94 (m, 8.0 Hz, 4H), 4.66 – 4.45 (m, 2H), 3.91 – 3.75 (m, 2H), 2.34 (s, 6H).
2H), 3.75 (s, 6H). 13C NMR (126 MHz, CDCl3) δ 199.05, 159.86, MS(ESI): m/z=535.1 [M+Na]+. The NMR spectra were consistent
143.05, 135.66, 133.45, 129.75, 128.85, 128.54, 119.70, 113.08, with literature values.3c
112.64, 55.17, 47.82, 47.60. HRMS (ESI) calcd. for [M+Na]+: C32 H28
Na O4: 499.1880. Found: 499.1863.
DL-((1R,2R,3S,4S)-3,4-bis(4-bromophenyl)cyclobutane-1,2-
diyl)bis((4-chlorophenyl)methanone) (2n). (E)-3-(4-bromophenyl)-1-
(4-chlorophenyl)prop-2-en-1-one (0.188 g, 0.5 mmol), and t-Bu-
DL-((1R,2R,3S,4S)-3,4-bis(4-bromophenyl)cyclobutane-1,2-
diyl)bis(phenylmethanone)
(2h).
(E)-3-(4-bromophenyl)-1- 4CzIPN (0.006 g, 1 mol%) in 1,4-dioxane (5 mL) gave 2n. Eluted with
phenylprop-2-en-1-one (0.143 g, 0.5 mmol), and t-Bu-4CzIPN (0.006 hexane/ethyl acetate = 95:5 to afford the desired major isomer
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g, 1 mol%) in 1,4-dioxane (5 mL) gave 2h. Eluted with hexane/ethyl product. 0.103, 55% yield, white solid. H NMR (500 MHz, CDCl3) δ
acetate = 95:5 to afford the desired major isomer product. 87.2 mg, 7.76 (d, J = 8.6 Hz, 4H), 7.61 (d, J = 8.2 Hz, 4H), 7.42 (d, J = 8.1 Hz,
6 | J. Name., 2012, 00, 1-3
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