C. Santi et al. / Tetrahedron 68 (2012) 10530e10535
10535
B.; Niggemann, M. J. Org. Chem. 2005, 70, 2402e2405; (k) Ho, C. M.; Yu, W.-Y.;
Che, C.-M. Angew. Chem. 2004, 116, 3365e3369 Angew. Chem. Int. Ed. 2004, 43,
3303e3307; (l) Oldenburg, P. D.; Que, L. Catal. Today 2006, 117, 15e21; (m)
Batile, C. J. R.; Donohoe, T. Chem. Soc. Rev. 2011, 40, 114e128.
(47), 71 (100), 55 (50). Anal. calcd for C10H20O2: C, 69.72; H, 11.70.
Found: C, 69.89; H, 11.73. [
a
]
28þ15.3 (c 1.70, CHCl3).
D
4.3.2. (1S,2S)-2-Methoxy-2-methylcyclohexanol (anti-6b). Oil, 1H
5. Woodward, R. B.; Brutcher, F. V. J. Am. Chem. Soc. 1958, 80, 209e211.
ꢀ
NMR (400 MHz, 298 K)
d
¼3.70 ppm (dd, 1H, 3JH,H¼3.0 and 10.1 Hz,
6. Prevost, C. Compt. Rend. 1933, 196, 1129e1131.
7. Santi, C.; Tiecco, M.; Testaferri, L.; Tomassini, C.; Santoro, S.; Bizzoca, G. Phos-
phorus, Sulfur, Silicon Relat. Elem. 2008, 183, 956e960.
8. Gogoi, P.; Sharma, S. D.; Konvar, D. Lett. Org. Chem. 2007, 4, 249e252.
9. Santoro, S.; Santi, C.; Sabatini, M.; Testaferri, L.; Tiecco, M. Adv. Synth. Catal.
2008, 350, 2881e2884.
10. (a) Wirth, T. Tetrahedron 1999, 55, 1e28; (b) Tiecco, M.; Testaferri, L.; Bagnoli, L.;
Marini, F.; Santi, C.; Temperini, A.; Scarponi, C.; Sternativo, S.; Terlizi, R.;
Tomassini, C. Arkivoc 2006, 186e206; (c) Tiecco, M.; Testaferri, L.; Bagnoli, L.;
Purgatorio, V.; Temperini, A.; Marini, F.; Santi, C. Tetrahedron: Asymmetry 2001,
12, 3297e3304; (d) Tiecco, M.; Testaferri, L.; Santi, C.; Tomassini, C.; Marini, F.;
Bagnoli, L.; Temperini, A. Eur. J. Org. Chem. 2000, 3451e3457.
11. (a) Freudendahl, D. M.; Santoro, S.; Shahzad, S. A.; Santi, C.; Wirth, T. Angew.
Chem., Int. Ed. 2009, 48, 8409e8411; (b) Santi, C.; Santoro, S.; Battistelli, B. Curr.
Org. Chem. 2010, 14, 2442e2462.
12. Grieco, P. A.; Yokoyama, Y.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1977, 42,
2034e2036.
13. Bhabak, K. P.; Mugesh, G. Chem.dEur. J. 2008, 14, 8640e8651.
14. Moussou, P.; Archelas, A.; Baratti, J.; Furstoss, R. J. Org. Chem. 1998, 63,
3532e3537.
15. (a) Santi, C.; Santoro, S.; Battistelli, B.; Testaferri, L.; Tiecco, M. Eur. J. Org. Chem.
2008, 5387e5390; (b) Battistelli, B.; Testaferri, L.; Tiecco, M.; Santi, C. Eur. J. Org.
Chem. 2011, 1848e1851; (c) Santoro, S.; Battistelli, B.; Testaferri, L.; Tiecco, M.;
Santi, C. Eur. J. Org. Chem. 2009, 4921e4925; (d) Santi, C.; Battistelli, B.;
Testaferri, L.; Tiecco, M. Green. Chem. 2012, 14, 1277e1280; (e) Santi, C.;
Santoro; Testaferri, L.; Tiecco, M. Synlett 2008, 1471e1474; (f) Tidei, C.; Piroddi,
M.; Galli, F.; Santi, C. Tetrahedron Lett. 2012, 53, 232e234.
CHOH), 3.23 (s, 3H, OCH3), 2.32 (br s, 1H, OH), 1.95e1.77 (m, 2H,
CH2), 1.73e1.57 (m, 2H, CH2), 1.45e1.25 (m, 4H, 2CH2), 1.16 (s, 3H,
CH3). 13C NMR (100.62 MHz, 298 K)
d
¼77.8 ppm (Cq), 75.0 (CHOH),
48.4 (OCH3), 32.9 (CH2), 30.0 (CH2), 23.4 (CH2), 22.0 (CH2), 15.3
(CH3). GCeMS (70 eV): m/z (%) 144 (23) [Mþ], 112 (5), 85 (100), 72
(39), 55 (27). Anal. Calcd for C8H16O2: C, 66.63; H, 11.18. Found: C,
29
66.32; H, 11.01. [
a
]
¼þ3.01 (c 1.13, CHCl3).
D
4.3.3. (1S,2S)-2-Methoxy-2-methylcyclopentanol (anti-6c). Oil, 1H
NMR (400 MHz, 298 K)
d
3.9 (t, 1H, 3JH,H¼6.0 Hz, CHOH), 3.23 (s, 3H,
OCH3), 2.15e2.06 (m,1H, CHH), 2.05 (br s,1H, OH),1.84e1.74 (m,1H,
CHH), 1.70e1.45 (m, 4H, 2CH2), 1.24 (s, 3H, CH3) ppm 13C NMR
(100.62 MHz, 298 K)
d
¼85.4 (Cq), 78.7 (CHOH), 50.2 (OCH3), 33.4
(CH2), 31.9 (CH2), 19.4 (CH2), 16.5 (CH3) ppm GCeMS (70 eV): m/z
(%) 130 (15) [Mþ], 115 (9), 98 (67), 85 (100), 72 (41), 55 (41). Anal.
Calcd for C7H14O2: C, 64.58; H, 10.84. Found: C, 64.45; H, 10.90.
29
[
a]
¼ꢀ3.79 (c 1.19, CHCl3).
D
4.3.4. (R)-2-Amino-3-(hydroperoxyseleninyl)propanoic acid. 1H
3
NMR (400 MHz, 298 K)
d
4.21 (dd, 1H, JH,H¼11.6 and 6.4 Hz),
16. Bhor, S.; Tse, M. K.; Klawonn, M.; Dobler, C.; Magerlein, W.; Beller, M. Adv. Synth.
Catal. 2004, 346, 263e267.
3.35 (t, 1H, JH,H¼2JH,H 11,6 Hz), 3.13 ppm (dd, 1H, JH,H¼11.6 Hz
3
2
and 3JH,H¼6.4 Hz) ppm 13C NMR (100.62 MHz)
¼172.2 (Cq), 53.4
d
17. (a) Tamura, Y.; Annoura, H.; Kondo, H.; Fuji, M.; Yashida, T.; Fujioka, H. Chem.
Pharm. Bull. 1987, 6, 2305e2313; (b) Juntilla, M. K.; Hormi, O. E. O. J. Org. Chem.
2004, 69, 4816e4820; (c) Rosatella, A. A.; Alfonso, C. A. M. Adv. Synth. Catal.
2001, 353, 2920e2926; (d) Juntilla, M. K.; Hormi, O. E. O. J. Org. Chem. 2009, 74,
3038e3047.
(CH), 49.5 (CH2)ppm 77Se NMR (76 MHz)
d 1204 ppm.
Acknowledgements
18. Niidu, A.; Paji, A.; Eek, M.; Muurisepp, A.-M.; Pehk, T.; Lopp, M. Tetrahedron:
Asymmetry 2006, 2678e2683.
The authors are particularly greatful to Dr. Roccaldo Sardella and
Mrs. Ianni for the HPLC analysis. We thanks also Dr. Francesco
Venturoni for a number of stimulating discussions. Italian British
partnership from British Council-CRUI (project Novel Catalysts for
Green Chemistry), financial support from M.I.U.R. (Ministero Ital-
19. (a) Natalini, B.; Sardella, R.; Macchiarulo, A.; Pellicciari., R. J. Sep. Sci. 2008,
31, 696e704; (b) Zheng, H.; Reetz, M. T. J. Am. Chem. Soc. 2010, 132,
15744e15751.
20. (a) (1S,2S)-anti 2b [
a
]
D
28þ22.17 (c 0.63, EtOH) see Ref. Kita, Y.; Yashida, Y.;
Mihara, S.; Furukawa, A.; Higuchi, K.; Fang, D. F.; Fujioka, H. Tetrahedron 1998,
54, 14689e14704 and 17a; Archer, I. V. J.; Leak, D. J.; Widdwson, D. A. Tetra-
hedron Lett. 1996, 37, 8819e8822; (b) (1S,2S)-anti 2c [
a
]
28þ17.02 (c 0.60, EtOH)
D
ꢀ
iano Universita e Ricerca), National Projects PRIN2007 Fondazione
assigned on the basis of the structural analogies with 1b and 2b. (c) (S)-2-
Phenyl-1,2-propanediol 2e [
a
]
28þ3.71 (c 0.63, CH2Cl2) see: Dobler, C.; Mehl-
Cassa di Risparmio: Project ‘Processi ecosostenibili per la produ-
D
tretter, G. M.; Sundermeier, U.; Beller, M. J. Organomet. Chem. 2001, 621, 70e76;
(d) In Ref. 9 based on a misinterpretation of the proton NMR data we wrongly
reported the product anti 2b as the syn isomer (1RS,2SR)-1-methylcyclo-
hexane-1,2-diol.
zione
e
l’analisi di molecole di interesse farmaceutico’.
2012.0114.021, are gratefully acknowledged.
References and notes
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