Enantioselective ring opening of meso-epoxides with tetrachlorosilane catalyzed by chiral bipyridine N,N′-dioxide derivatives

Tetrahedron Letters

Volumn 43, Issue 49, 2002, Pages 8827-8829

  Nakajima, Makoto ^a   Saito, Makoto ^a   Uemura, Michinao ^a   Hashimoto, Shunichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIPYRIDINE DERIVATIVE; CHLOROHYDRIN DERIVATIVE; EPOXIDE; ETHYLAMINE; ETHYLDIISOPROPYLAMINE; SILANE DERIVATIVE; SILICON TETRACHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; RING OPENING; SYNTHESIS;

EID: 0037010822     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02229-3     Document Type: Article

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22. R (1S,2S)-(+)-isomer, 22.0 min (95.1%); (1R,1R)-(-)-isomer, 24.0 min (4.9%).
23. Fu and co-workers reported that the presence of diisopropylethylamine is important for higher enantioselectivity and more reproducible results.
24. 12 revealed that dissociation of N-oxide from the product is so fast that the benefit of ligand exchange by diisopropylethylamine is negligible.
25. 1H NMR spectrum before the addition of diisopropylethylamine and the signals of the free N,N′-dioxide appeared upon the addition of amine. On the other hand, the free N,N′-dioxide was observed in the epoxide opening even in the absence of amine.
26. 3)). Absolute configurations of 8 and 9 have not been determined.