The first preparation of (1S,5R)-(−)- and (1R,5S)-(+)-7-phenyl-3-borabicyclo[3.3.1]non-6-enes and their application for synthesis of chiral cyclohexene derivatives |
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| Authors: | ME Gurskii AV Ignatenko MYu Antipin |
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| Institution: | a N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, GSP-1, Leninsky prosp., 47, Moscow, Russia
b A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991, Vavilova str., 28, Moscow, Russia |
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| Abstract: | (1S,5R)-(−)- and (1R,5S)-(+)-7-phenyl-3-borabicyclo3.3.1]non-6-enes of 97-98% de that differed only by the location of the double bond were prepared by the resolution of diastereomeric intramolecular chelates with l- and d-prolinol. Deboronation of chiral bicyclic boranes obtained was used for synthesis of optically active 3,5-dimethyl- and 3,5-dihydroxymethyl-1-phenylcyclohexenes. |
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| Keywords: | 3-Borabicyclo[3 3 1]non-6-ene derivatives 2 2-Disubstituted 3-borabicyclo[3 3 1]-nonanes Chiral auxiliaries Chelate complexes Diastereomeric purity |
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