Catalytic enantioselective epoxidation of homoallylic alcohols by chiral zirconium complexes

Organic Letters

Volumn 5, Issue 1, 2003, Pages 85-87

  Okachi, Takahiro ^a   Murai, Norio ^a   Onaka, Makoto ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALLYL COMPOUND; LIGAND; TARTARIC ACID DERIVATIVE; TARTRAMIDE; UNCLASSIFIED DRUG; ZIRCONIUM DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; COMPLEX FORMATION; ENANTIOSELECTIVITY; EPOXIDATION;

EID: 0041426054     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027261t     Document Type: Article

References (26)

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14. Experimental details are provided in Supporting Information.
15. In this paper, we referred to Zr/ligand ratios (or mixtures) of 0.2/0.22 and 0.2/0.41 as 1:1 and 1:2, respectively.
16. Diethyl tartrate, dibenzyl tartrate, and dibenzyl tartramide were unusable as ligands in the 1:2 system.
17. It has been reported that enantiofacial selectivities were reversed between 1:1 and 2:1 (not 1:2) ratios of Ti/tartramide in the epoxidation of allylic alcohols: Lu, L. D.; Johnson, R. A.; Finn, M. G.; Sharpless, K. B. J. Org. Chem. 1984, 49, 728.
18. Inversion of enantiofacial selection was also observed in stoichiometric systems of entries 1 and 3 in Table 1.
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26. Absolute configuration of 2e was determined by comparing the chiral HPLC spectrum after transformation to compound 3: (a) Takemoto, T.; Nishi, T. Tetrahedron Lett. 2000, 41, 1785. (b) Nishi, T.; Ishibashi, K.; Takemoto, T.; Nakajima, K.; Fukazawa, T.; Iio, K.; Mukaiyama, O.; Yamaguchi, T. Bioorg. Med. Chem. Lett. 2000, 10, 1665.