RSC Advances
Paper
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2
3
H), 7.72 (d, J ¼ 8.0 Hz, 1H), 7.48–7.51 (m, 1H), 7.38–7.39 (m,
H), 6.79 (s, 1H), 6.75 (s, 1H), 4.53 (s, 2H), 2.38 (s, 3H), 1.80 (s,
H). The spectroscopic data are in good agreement with those
O. Hucke, ChemMedChem, 2011, 6, 505–513; (f) J. Clayden,
W. J. Moran, P. J. Edwards and S. R. LaPlante, Angew.
Chem., Int. Ed., 2009, 48, 6398–6401.
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reported. Its optical purity (97% ee) was determined by HPLC
analysis at 20 C using a CHIRALPAK AD-3 column (hexanes/2-
2 For reviews, see: (a) S. S. Yu and L. Pu, Tetrahedron, 2015, 71,
745–772; (b) M. Shibasaki and S. Matsunaga, in Privileged
Chiral Ligands and Catalysts, ed. Q.-L.Zhou, Wiley-VCH,
Weinheim, 2011, pp. 295–332; (c) J. M. Brunel, Chem. Rev.,
2007, 107, PR1–PR45; (d) Y. Chen, S. Yekta and
A. K. Yudin, Chem. Rev., 2003, 103, 3155–3211; (e)
P. Kocovsky, S. Vyskocil and M. Smrcina, Chem. Rev., 2003,
103, 3213–3245.
3 For general reviews on the asymmetric synthesis of
atropoisomeric biaryls, see: (a) Y. B. Wang and B. Tan, Acc.
Chem. Res., 2018, 51, 534–547; (b) P. Renzi, Org. Biomol.
Chem., 2017, 15, 4506–4516; (c) P. Loxq, E. Manoury,
R. Poli, E. Deydier and A. Labande, Coord. Chem. Rev.,
2016, 308, 131–190; (d) J. Wencel-Delord and F. Colobert,
Synthesis, 2016, 48, 2981–2996; (e) S. Shirakawa, S. Y. Liu
and S. Kaneko, Chem. – Asian J., 2016, 11, 330–341; (f)
J. Wencel-Delord, A. Panossian, F. R. Leroux and
F. Colobert, Chem. Soc. Rev., 2015, 44, 3418–3430; (g)
D. Zhang and Q. R. Wang, Coord. Chem. Rev., 2015, 286, 1–
16; (h) G. Y. Ma and M. P. Sibi, Chem.–Eur. J., 2015, 21,
11644–11657; (i) G. Bencivenni, Synlett, 2015, 1915–1922; (j)
G. Bringmann, T. Gulder, T. A. M. Gulder and
M. Breuning, Chem. Rev., 2011, 111, 563–639; (k)
G. Bringmann, A. J. P. Mortimer, P. A. Keller, M. J. Gresser,
J. Garner and M. Breuning, Angew. Chem., Int. Ed., 2005,
44, 5384–5427.
ꢂ
ꢄ1
propanol ¼ 85 : 15; ow rate: 1.0 mL min ; retention times:
8.8 min (R), 11.2 min (S)).
Table 6, entry 4. Following procedure C described above,
(
4
ꢁ)-4b (27.8 mg, 0.10 mmol) was converted to (R)-5b (15.7 mg,
9% yield, 93% ee) and (S)-4b (14.2 mg, 51% yield, 98% ee), aer
purication of the crude reaction mixture by ash column
chromatography (hexanes : EtOAc ¼ 8 : 1).
(
R)-(1-(2-Hydroxy-3,6-dimethylphenyl)naphthalen-2-yl)methyl
2
1
1
acetate (R)-5b. Colorless oil; [a]
D
3
ꢄ 13.7 (c 0.51, CHCl ); H-NMR
(400 MHz, CDCl
3
) d 7.96 (d, J ¼ 8.5 Hz, 1H), 7.91 (d, J ¼ 8.0 Hz,
1
2
1
2
1
1
1
H), 7.63 (d, J ¼ 8.0 Hz, 1H), 7.50–7.54 (m, 1H), 7.35–7.42 (m,
H), 7.14 (d, J ¼ 7.5 Hz, 1H), 6.84 (d, J ¼ 7.5 Hz, 1H), 4.99 (d, J ¼
2.5 Hz, 1H), 4.94 (d, J ¼ 12.5 Hz, 1H), 4.58 (s, 1H), 2.28 (s, 3H),
1
3
.04 (s, 3H), 1.78 (s, 3H); C-NMR (100 MHz, CDCl ) d 170.8,
3
51.3, 135.3, 133.6, 133.2, 132.4, 132.3, 130.6, 129.1, 128.2,
27.1, 126.7, 126.2, 125.5, 122.7, 121.9, 121.7, 64.8, 20.8, 19.6,
6.0; IR (CHCl
ꢄ1
3
) n 3553, 1737 cm ; HRMS (MALDI) m/z calcd for
+
C
21
H
20
O
3
Na [M + Na] : 343.1310, found: 343.1305. Its optical
ꢂ
purity (93% ee) was determined by HPLC analysis at 20 C using
a CHIRALPAK AD-3 column (hexanes/2-propanol ¼ 95 : 5; ow
ꢄ1
rate: 1.0 mL min ; retention times: 8.5 min (S), 10.6 min (R)).
(
S)-2-(2-(Hydroxymethyl)naphthalen-1-yl)-3,6-dimethylphenol
2
1
14
20
(S)-4b. Colorless oil; [a]D + 21.7 (c 0.6, CHCl ) (lit. [a]D + 27.2 (c
3
1
0.4, CHCl
3
) for (S)-4b with 87% ee); H-NMR (500 MHz, CDCl
3
)
d 7.98 (d, J ¼ 8.5 Hz, 1H), 7.91 (d, J ¼ 8.0 Hz, 1H), 7.75 (d, J ¼
4 For reviews, see: (a) M. Klussmann and D. Sureshkumar,
Synthesis, 2011, 353–369; (b) H. Wang, Chirality, 2010, 22,
827–837; (c) M. C. Kozlowski, B. J. Morgan and
E. C. Linton, Chem. Soc. Rev., 2009, 38, 3193–3207. For
selected examples, see: (d) H. Y. Kim, S. Takizawa, H. Sasai
and K. Oh, Org. Lett., 2017, 19, 3867–3870; (e) S. Narute,
R. Parnes, F. D. Toste and D. Pappo, J. Am. Chem. Soc.,
2016, 138, 16553–16560; (f) H. Egami, K. Matsumoto,
T. Oguma, T. Kunisu and T. Katsuki, J. Am. Chem. Soc.,
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.5 Hz, 1H), 7.49–7.52 (m, 1H), 7.34–7.41 (m, 2H), 7.16 (d, J ¼
.5 Hz, 1H), 6.86 (d, J ¼ 7.5 Hz, 1H), 4.52 (s, 2H), 2.29 (s, 3H),
.79 (s, 3H). The spectroscopic data are in good agreement with
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those reported. Its optical purity (98% ee) was determined by
ꢂ
HPLC analysis at 20 C using a CHIRALPAK AD-3 column
ꢄ1
(
hexanes/2-propanol ¼ 90 : 10; ow rate: 1.0 mL min ; reten-
tion times: 12.9 min (R), 29.8 min (S)).
2
010, 132, 13633–13635; (g) H. Egami and T. Katsuki, J. Am.
Conflicts of interest
Chem. Soc., 2009, 131, 6082–6083; (h) S. Takizawa,
T. Katayama, C. Kameyama, K. Onitsuka, T. Suzuki,
T. Yanagida, T. Kawai and H. Sasai, Chem. Commun., 2008,
There are no conicts to declare.
1
810–1812; (i) J. B. Hewgley, S. S. Stahl and
Acknowledgements
M. C. Kozlowski, J. Am. Chem. Soc., 2008, 130, 12232–
12233; (j) Q. X. Guo, Z. J. Wu, Z. B. Luo, Q. Z. Liu, J. L. Ye,
S. W. Luo, L. F. Cun and L. Z. Gong, J. Am. Chem. Soc.,
2007, 129, 13927–13938; (k) X. L. Li, J. B. Hewgley,
C. A. Mulrooney, J. M. Yang and M. C. Kozlowski, J. Org.
Chem., 2003, 68, 5500–5511; (l) M. Nakajima, I. Miyoshi,
K. Kanayama, S. Hashimoto, M. Noji and K. Koga, J. Org.
Chem., 1999, 64, 2264–2271; (m) M. Smrcina, J. Polakova,
S. Vyskocil and P. Kocovsky, J. Org. Chem., 1993, 58, 4534–
4538.
This research was supported by JSPS KAKENHI [grant numbers:
1
1
6H01151/18HO4411 (Middle Molecular Strategy) and
8H02556] and AMED (grant number 18am0101084j0002). We
acknowledge Toyobo Co. Ltd. for supplying LIP301.
Notes and references
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(a) S. T. Toenjes and J. L. Gustafson, Future Med. Chem., 2018,
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2
0, 409–422; (b) P. W. Glunz, Bioorg. Med. Chem. Lett., 2018,
8, 53–60; (c) J. E. Smyth, N. M. Butler and P. A. Keller, Nat.
5 For instances, see: (a) S. C. Lu, S. B. Poh and Y. Zhao, Angew.
Chem., Int. Ed., 2014, 53, 11041–11045; (b) G. Y. Ma, J. Deng
and M. P. Sibi, Angew. Chem., Int. Ed., 2014, 53, 11818–11821;
Prod. Rep., 2015, 32, 1562–1583; (d) A. Zask, J. Murphy and
G. A. Ellestad, Chirality, 2013, 25, 265–274; (e)
S. R. LaPlante, P. J. Edwards, L. D. Fader, A. Jakalian and
1174 | RSC Adv., 2019, 9, 1165–1175
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