Enantiotopic-Place Selective C-H Oxidation Using a (Salen)manganese(III) Complex as a Catalyst

Synlett

Volumn 1997, Issue 7, 1997, Pages 836-838

  Miyafuji, Akio ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013525731     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5780     Document Type: Article

References (23)

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2. For the recent review for asymmetric oxidation, see: a) In "Comprehensive Organic Synthesis" ed by Trost, B. M., Pergamon Press, Oxford, 1991, Vol. 7. b) In "Catalytic Asymmetric Synthesis" ed by Ojima, I., VCH, New York, 1993, Chapt. 4.
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17. 4-(t-Butyl)tetrahydropyran was synthesized according to the reported procedure: Bailey, W. F.; Bischoff, J. J. J. Org. Chem. 1985, 50, 3009-3010.
18. Chtorobenzene has been found to be the best solvent for asymmetric benzylic oxidation using (salen)manganese(III) complex as a catalyst (reference 2b).
19. Although compound 4 was a mixture of axial- and equatorial-isomers, the values of enantiomeric excess of these two isomers were equal.
20. Sobukawa, M.; Koga, K. Tetrahedron Lett. 1993, 34, 5101-5104.
21. Compound 11 was synthesized from cyclopentene-1,2-dicarboxylic acid which was prepared according to the reported procedure (reference 10), by the sequence: i) Fisher's esterification, ii) catalytic hydrogenation with Pd-C, iii) LAH reduction of the resulting diethyl cis-cyclopentane-1,2-dicarboxylate, and iv) heating the resulting diol in DMSO.
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