Construction of Optically Active CF3-Containing Quarternaly Carbon by Regiospecific SN2' Reactions.
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Accession number;02A0620411
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| Title;Construction of Optically Active CF3-Containing Quarternaly Carbon by Regiospecific SN2' Reactions. |
| Author;
KIMURA MITSUO
(Tokyo Inst. of Technology, Graduate School)
YAMAZAKI TAKASHI
(Tokyo Inst. of Technology, Graduate School)
KITAZUME TOMOYA
(Tokyo Inst. of Technology, Graduate School)
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Journal Title;Fusso Kagaku Toronkai Koen Yoshishu
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Journal Code:F0135B
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ISSN:
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VOL.25th;NO.;PAGE.30-32(2001)
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| Figure&Table&Reference; |
| Pub. Country;Japan |
| Language;Japanese |
| Abstract;Recently, we have reported that the CF3-containing allylic alcohol derivatives furnished the substitution products via the clean anti-SN2' mechanism when treated with an appropriate Grignard reagent in the presence of catalytic amounts of CuCN and TMSCl. Then, utilization of this reaction was planned for the construction of the title compounds as the further extension. In the first place, we have started with the trisubstituted racemle CF3-containing allylic derivatives which was subjected to various Grignard reagents. When Grignard reagents and the substrates contained less hindered n-alkyl groups, the exclusive formation of the SN2' products were observed. On the other hand, when either Grignard reagents or the substrate became bulkier, the SN2 and the defluorination products were yielded along with the SN2' products. This process with optically active substrates were found to give the desired SN2' products with high level of chirality transmission. (author abst.) |
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