TERPENE LIGANDS AS THE BASIS OF CATALYTIC SYSTEMS
883
presence of Ti(OPri)4 (0.031 g, 0.11 mmol), ligand
IV) (0.120 g, 0.22 mmol), and H2O (1.9 ml,
1.1 mmol) to yield 0.90 g (83%) of compound ( ).
]D +5.6 ( 1.0, EtOH); the enantiomeric excess was
28%.
12. Hogan, P.J., Hopes, P.A., Moss, W.O., Robinson, G.E.,
and Patel, I., Org. Proc. Res. Dev., 2002, vol. 6, no. 3,
pp. 225⎯229.
(
2
[α
c
13. Pitchen, P., France, C.J., McFarlane, I.M., Newton, C.G.,
and Thompson, D.M., Tetrahedron Lett., 1994, vol. 35,
no. 3, pp. 485⎯486.
(i) Sulfide (1) (0.5 g, 2.2. mmol) was oxidized by
CHP (0.86 ml, 2.2 mmol) in toluene (2.55 mol/l) in
the presence of Ti(OPri)4 (0.031 g, 0.11 mmol), ligand
14. Kubo, K., Oda, K., Kaneko, T., Satoh, H., and
Nohara, A., Chem. Pharm. Bull., 1990, vol. 38,
pp. 2853⎯2858.
(
V
) (0.071 g, 0.22 mmol), and H2O (1.9 ml, 1.1 mmol)
to yield 0.84 g (78%) of compound ( ). [ ]D +17.5
1.0, EtOH); the enantiomeric excess was 84%.
15. Nishide, K., Nakayama, A., and Kusumoto, T., Chem.
2
α
Lett., 1990, pp. 623 625.
⎯
(
c
16. Sintez sul’fidov, tiofenolov i tiolov tipa soedinenii, vstreꢀ
chayushchikhsya v neftyakh (Synthesis of Sulfides,
Thiophenols, and Thiols of the Type of Compounds
Occurring in Oils), Karaulov, E.N., Ed., Moscow, 1988.
(j) Sulfide ( ) (0.5 g, 2.2. mmol) was oxidized by
ClO2 (9.1 ml, 1.1 mmol) in toluene (0.12 mol/l) in the
presence of Ti(OPri)4 (0.031 g, 0.11 mmol), ligand (
(0.071 g, 0.22 mmol), and H2O (1.9 ml, 1.1 mmol) to
yield 0.90 g (84%) of compound ( ). [ ]D –5.3 ( 1.0,
1
V)
17. Lin, G., Cogan, D.A., and Ellman, J.A., J. Am. Chem.
2
α
c
Soc., 1997, vol. 119, no. 41, pp. 9913
⎯9917.
EtOH); the enantiomeric excess was 27%.
18. Kuchin, A.V., Rubtsova, S.A., and Loginova, I.V., Izv.
Akad. Nauk, Ser. Khim., 2001, no. 3, pp. 413 416.
⎯
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RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY Vol. 36
No. 7
2010