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2005
Enantioselective syntheses
O 0031
Ruthenium(salen)-Catalyzed Aerobic Oxidative Desymmetrization of meso-Diols
Its Kinetics. — The photoinduced oxidative desymmetrization of meso-diols, e.g.
36- 029 and
(III), is efficiently catalyzed by chiral nitrosylruthenium(salen) complexes (I) or (II) to
afford optically active lactols in good diastereoselectivities. The latter are directly converted to lactones, e.g. (V), in moderate to high enantioselectivity. A variety of cyclic
and acyclic substrates is desymmetrized using this method. The catalyst structure must
be fine-tuned for each single substrate. A detailed study of the kinetics of this reaction
is presented to explain the results obtained. — (SHIMIZU, H.; ONITSUKA, S.;
EGAMI, H.; KATSUKI*, T.; J. Am. Chem. Soc. 127 (2005) 15, 5396-5413; Dep.
Chem., Fac. Sci., Kyushu Univ., Higashi, Fukuoka 812, Japan; Eng.) — Mischke
2005
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