Beneficial effect of ortho-methoxy groups in the asymmetric ring opening of meso epoxides with silicon tetrachloride catalyzed by chiral ortho-methoxyophenyl-diazaphosphonamide Lewis bases

Angewandte Chemie - International Edition

Volumn 39, Issue 14, 2000, Pages 2554-2557

  Brunel, Jean Michel ^a   Legrand, Olivier ^a   Reymond, Sébastien ^a   Buono, Gérard ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Asymmetric catalysis; Catalysts; Lewis bases; Phosphorous; Ring opening

Indexed keywords

EPOXIDE; SILICON DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; SYNTHESIS;

EID: 0034679520     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000717)39:14<2554::AID-ANIE2554>3.0.CO;2-1     Document Type: Article

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37. 3. A total of 1925 reflections were measured at T = 298 K. The standards were measured after every 25 reflections. Among the first 20 pairs of reflections, the signs of the corresponding calculated differences established that the molecule is described with the correct S absolute configuration. Moreover, the sum of the bond angles around the nitrogen atom of the pyrrolidine ring is 338.1, showing a nonplanar configuration. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-140554. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam. ac.uk).
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45. 3). Moreover, the chlorohydrin generated in entry 11 is not very stable and a decomposition of the product has been noticed after few hours.
46. 4 catalyzed by the chiral ortho-methoxyphenyldiazaphosphonamide Lewis bases. Whatever the experimental conditions, low enantiomeric excess values of chlorohydrins (<10% ee) and poor regioselectivity have been encountered, except when opening racemic phenyloxirane, where a total regioselectivity has been observed but with only 12% ee. The residual epoxide was isolated in 35% yield and 20% ee.