ꢀ
S.V. Slungard et al. / Tetrahedron 67 (2011) 5642e5650
5650
8.06 (d, J¼8.4, 1H), 7.94e7.89 (m, 2H), 7.83 (d, J¼7.1, 1H), 7.59e7.52
(m, 3H), 5.90 (m, 1H), 2.61 (d, J¼4.8, 1H, OH).
References and notes
1. Ikariya, T.; Blacker, A. J. Acc. Chem. Res. 2007, 40, 1300e1308.
2. Gladiali, S.; Alberico, E. Chem. Soc. Rev. 2006, 35, 226e236.
3. Hayes, A. M.; Morris, D. J.; Clarkson, G. J.; Wills, M. J. Am. Chem. Soc. 2005, 127,
7318e7319.
4. Wu, X.; Li, X.; Zanotti-Gerosa, A.; Pettman, A.; Liu, J.; Mills, A. J.; Xiao, J. Chem.dEur.
J. 2008, 14, 2209e2222.
5. Wu, X.; Xiao, J. Chem. Commun. 2007, 2449e2466.
6. Wu, X.;Liu,J.;Tommaso,D.D.;Iggo,J. A.;Catlow, C. R.A.;Bacsa,J.;Xiao,J.Chem.dEur.
J. 2008, 14, 7699e7715.
7. Petra, D. G. I.; Reek, J. N. H.; Handgraaf, J. W.; Meijer, E. J.; Dierkes, P.; Kamer, P.
C. J.; Brussee, J.; Schoemaker, H. E.; Van Leeuwen, P. W. N. M. Chem.dEur. J.
2000, 6, 2818e2829.
4.5.11. (R)-1-(Naphthalen-1-yl)propan-1-ol (24)50. A reference
compound was prepared as described for 20 starting with 1-
(naphthalen-1-yl)propan-1-one (12) (230 mg, 1.25 mmol). This
gave after silica-gel column chromatography (hexane/EtOAc, 2/1,
Rf¼0.28) (R)-24 as an oil, 60 mg (0.32 mmol, 26%), ee¼78.0%, ½a D20
ꢃ
þ61.6 (c 0.50, benzene), lit.51 ee¼77%, ½a D18
þ61.1 (c 0.44, benzene).
ꢃ
1H NMR (300 MHz, CDCl3)
d
: 8.11 (d, J¼9.3, 1H), 7.86 (d, J¼7.2, 1H),
7.77 (d, J¼8.1, 1H), 7.63 (d, J¼7.1, 1H), 7.53e7.46 (m, 3H), 5.42 (m,
1H), 2.04e1.91 (m, 3H), 1.04 (t, J¼7.4, 3H).
8. Chen, Y.; Liu, S.; Lei, M. J. Phys. Chem. C 2008, 112, 13524e13527.
9. Chen, Y.; Tang, Y.; Liu, S.; Lei, M.; Fang, W. Organometallics 2009, 28,
2078e2084.
4.5.12. (R)-1-(Naphthalen-1-yl)ethyl benzoate (25)52. To a mixture
of (R)-1-(naphthalen-1-yl)ethanol (20) (517 mg, 3.00 mmol) and
NEt3 (1.37 g, 13.53 mmol) in CH2Cl2 (20 mL) at 0 ꢁC was added
benzoyl chloride (0.67 g, 4.77 mmol). After stirring for 12 h at room
temperature, brine (25 mL) was added, and the mixture was
extracted with diethyl ether (3ꢂ25 mL). The combined organic
fraction was washed with aq HCl soln (5%, 3ꢂ15 mL), brine (25 mL)
and satd aq NaHCO3 (25 mL). Drying over Na2SO4, concentration in
vacuum, and silica-gel column chromatography (hexane/EtOAc, 4/
1, Rf¼0.47), gave 334 mg (1.21 mmol, 40%) of a clear oil, ee¼98%,
10. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc.
1996, 118, 2521e2522.
11. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97e102.
12. Yamakawa, M.; Yamada, I.; Noyori, R. Angew. Chem., Int. Ed. 2001, 40,
2818e2821.
13. Noyori, R.; Yamakawa, M.; Hashiguchi, S. J. Org. Chem. 2001, 66, 7931e7944.
14. Brandt, P.; Roth, P.; Andersson, P. G. J. Org. Chem. 2004, 69, 4885e4890.
15. Fuglseth, E.; Sundby, E.; Hoff, B. H. J. Fluorine Chem. 2009, 130, 600e603.
16. Sterk, D.; Stephan, M.; Mohar, B. Org. Lett. 2006, 8, 5935e5938.
17. Gamez, P.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705e718.
18. von Arx, M.; Mallat, T.; Baiker, A. Tetrahedron: Asymmetry 2001, 12, 3089e3094.
19. Ramachandran, P. V.; Teodorovic, A. V.; Brown, H. C. Tetrahedron 1993, 49,
1725e1738.
20. Yong, K. H.; Chong, J. M. Org. Lett. 2002, 4, 4139e4142.
21. Matsuda, T.; Harada, T.; Nakajima, N.; Itoh, T.; Nakamura, K. J. Org. Chem. 2000,
65, 157e163.
22. Ohkuma, T.; Koizumi, M.; Doucet, H.; Pham, T.; Kozawa, M.; Murata, K.; Ka-
tayama, E.; Yokozawa, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1998, 120,
13529e13530.
½
a 2D5
ꢃ
ꢀ101.8 (c 1.00, EtOH). CD (MeCN): D3¼ꢀ12.6 (223 nm). 1H
NMR (300 MHz, CDCl3)
d: 8.18 (d, J¼8.2, 1H), 8.10 (m, 2H), 7.87 (m,
1H), 7.80 (d, J¼8.3, 1H), 7.70 (d, J¼7.1, 1H), 7.60e7.42 (m, 6H), 6.90
(q, J¼6.6, 1H), 1.85 (d, J¼6.6, 3H).
23. Goushi, S.; Funabiki, K.; Ohta, M.; Hatano, K.; Matsui, M. Tetrahedron 2007, 63,
4061e4066.
24. Mallat, T.; Bodmer, M.; Baiker, A. Catal. Lett. 1997, 44, 95e99.
25. Fuglseth, E.; Thvedt, T. H. K.; Førde Møll, M.; Hoff, B. H. Tetrahedron 2008, 64,
7318e7323.
26. Thvedt, T. H. K.; Fuglseth, E.; Sundby, E.; Hoff, B. H. Tetrahedron 2009, 65,
9550e9556.
27. Thvedt, T. H. K.; Fuglseth, E.; Sundby, E.; Hoff, B. H. Tetrahedron 2010, 66,
6733e6743.
28. Hanch, C.; Leo, A.; Hoekman, D. Exploring QSAR-Hydrophobic, Electronic and
Steric Constants; ACS Professional Reference Book; American Chemical Society:
Washington, DC, 1995.
29. Wu, X.; Li, X.; Hems, W.; King, F.; Xiao, J. Org. Biomol. Chem. 2004, 2, 1818e1821.
30. Liu, W.; Cui, X.; Cun, L.; Zhu, J.; Deng, J. Tetrahedron: Asymmetry 2005, 16,
2525e2530.
31. Sinnokrot, M. O.; Sherrill, C. D. J. Am. Chem. Soc. 2004, 126, 7690e7697.
32. Meyer, E. A.; Castellano, R. K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42,
1210e1250.
33. Wu, X.; Vinci, D.; Ikariya, T.; Xiao, J. Chem. Commun. 2005, 4447e4449.
34. Bervova, N.; Nakanishi, K. Circular dichroism. Principles and Applications In.
Exciton Chirality Method: Principles and Applications; Berova, N., Nakanishi, K.,
Woody, R. W., Eds.; Wiley-VCH: New York, NY, 2000; pp 337e382.
35. Harada, N.; Nakanishi, K. Circular Dichroism Spectroscopy. Exciton Coupling in
Organic Stereochemistry; University Science Books: Mill Valley, 1983; 1e460.
36. Adam, W.; Lukacs, Z.; Viebach, K.; Humpf, H. U.; Saha-Moeller, C. R.; Schreier, P.
J. Org. Chem. 2000, 65, 186e190.
37. Berova, N.; Di Bari, L.; Pescitelli, G. Chem. Soc. Rev. 2007, 36, 914e931.
38. Fuglseth, E.; Ottherholt, E.; Høgmoen, H.; Sundby, E.; Charnock, C.; Hoff, B. H.
Tetrahedron 2009, 65, 9807e9813.
39. Verniest, G.; Van Hende, E.; Surmont, R.; De Kimpe, N. Org. Lett. 2006, 8,
4767e4770.
4.5.13. (S)-2-Fluoro-1-(naphthalen-1-yl)ethyl benzoate (26). The
synthesis was performed as described for 25, starting with (S)-21
(105 mg, 0.55 mmol). This gave 120 mg (0.41 mmol, 74%) of a white
solid, mp 74e75 ꢁC, Rf¼0.41, ee¼89.0%, ½a 2D0
ꢀ171.6 (c 1.00, EtOH),
ꢃ
CD (MeCN): D3¼ꢀ28.8 (227 nm). 1H NMR (400 MHz, CDCl3)
d: 8.25
(d, J¼8.8, 1H), 8.16 (m, 2H), 7.89 (d, J¼8.4, 1H), 7.85 (d, J¼8.0, 1H),
7.69 (d, J¼6.8, 1H), 7.64e7.58 (m, 2H), 7.54 (m, 1H), 7.51e7.46 (m,
3H), 7.14e7.07 (m, 1H), 4.90 (ddd, J¼48.1, 10.5, 7.8, 1H), 4.83 (ddd,
J¼46.6, 10.5, 3.0, 1H). 13C NMR (100 MHz, CDCl3)
d: 165.6, 133.8,
133.3, 131.0, 130.4, 129.8 (2C), 129.8, 129.4, 129.1, 128.5 (2C), 126.9,
126.0, 125.3, 124.7, 122.6, 84.8 (d, J¼180.1), 72.1 (d, J¼21.1). 19F NMR
(376 MHz, CDCl3)
d
: ꢀ220.2 (dt, J¼47.4, 15.9, 1F). HRMS (EI):
294.1059 (calcd 294.1051, Mþ). IR (KBr, cmꢀ1): 3062, 1717, 1287,
1104.
4.5.14. (S)-2,2-Difluoro-1-(naphthalen-1-yl)ethyl benzoate (27). The
synthesis was performed as described for 25, starting with (S)-22
(110 mg, 0.53 mmol). Work up and purification by silica-gel column
chromatography (CH2Cl2/hexane, 4/1, Rf¼0.56) gave 140 mg
(0.45 mmol, 85%) of a white solid, mp 86e88 ꢁC, ee¼76.5% (based
on 22), ½a 2D5
ꢃ
ꢀ178.6 (c 1.09, EtOH), CD (MeCN): D3¼ꢀ28.0 (225). 1H
NMR (400 MHz, CDCl3)
d
: 8.24 (d, J¼8.4, 1H), 8.14 (m, 2H), 7.90 (d,
J¼7.6, 2H), 7.76 (d, J¼7.2, 1H), 7.65e7.59 (m, 2H), 7.57e7.47 (m, 4H),
7.00 (dt, 1H, J¼10.9, 4.2, 1H), 6.26 (dt, J¼55.2, 4.2, 1H). 13C NMR
40. Palmer, M. J.; Kenny, J. A.; Walsgrove, T.; Kawamoto, A. M.; Wills, M. J. Chem.
Soc., Perkin Trans. 1 2002, 416e427.
(100 MHz, CDCl3) d: 164.9, 133.8, 133.6, 131.1, 130.0, 129.9 (2C),
41. Bennett, M. A.; Smith, A. K. Dalton Trans. 1974, 233e241.
42. Fuglseth, E.; Sundby, E.; Bruheim, P.; Hoff, B. H. Tetrahedron: Asymmetry 2008,
19, 1941e1946.
43. Xu, Q.; Zhou, H.; Geng, X.; Chen, P. Tetrahedron 2009, 65, 2232e2238.
44. Zhao, H.; Qin, B.; Liu, X.; Feng, X. Tetrahedron 2007, 63, 6822e6826.
45. O’Shea, P. D.; Chen, C. Y.; Gauvreau, D.; Gosselin, F.; Hughes, G.; Nadeau, C.;
Volante, R. P. J. Org. Chem. 2009, 74, 1605e1610.
46. Nakamura, K.; Matsuda, T. J. Org. Chem. 1998, 63, 8957e8964.
47. Hughes, G.; O’Shea, P.; Goll, J.; Gauvreau, D.; Steele, J. Tetrahedron 2009, 65,
3189e3196.
48. Theisen, P. D.; Heathcock, C. H. J. Org. Chem. 1988, 53, 2374e2378.
49. Pirkle, W. H.; Hoekstra, M. S. J. Org. Chem. 1974, 39, 3904e3905.
50. Hatano, M.; Miyamoto, T.; Ishihara, K. J. Org. Chem. 2006, 71, 6474e6484.
51. Nakamura, Y.; Takeuchi, S.; Okumura, K.; Ohgo, Y. Tetrahedron 2001, 57,
5565e5571.
129.2, 129.0, 128.9 (t, J¼2.5), 128.5 (2C), 127.0, 126.2, 126.0, 125.2,
122.9, 114.1 (t, J¼246.3), 71.0 (t, J¼26.2). 19F NMR (376 MHz, CDCl3)
d
: ꢀ126.2 (dd, J¼55.5, 11.3, 1F), ꢀ126.4 (dd, J¼55.0, 10.2, 1F). HRMS
(EI): 312.0958 (calcd 312.0956, Mþ) IR (KBr, cmꢀ1): 3058, 1719,
1284, 1110.
Acknowledgements
The group is thankful to the Anders Jahres foundation for fi-
nancial support. Ingemund M.F. Engøy and Roger Aarvik are
thanked for their contributions. Susana Villa Gonzalez is acknowl-
edged for the HRMS experiments.
52. Suzuki, Y.; Muramatsu, K.; Yamauchi, K.; Morie, Y.; Sato, M. Tetrahedron 2005,
62, 302e310.