caa a22 4500 475761782 CHVBK 20180406123553.0 cr unu---uuuuu 170329e20000501xx s 000 0 eng 10.1007/BF02494718 doi (NATIONALLICENCE)springer-10.1007/BF02494718 Stereoselective synthesis of homoallylic alcohols of the [2.2]paracyclophane series and their use as auxiliaries in asymmetric allylboration of aldehydes [Elektronische Daten] [N. Vorontsova, V. Rozenberg, E. Vorontsov, O. Tok, Yu. Bubnov] Stereoselectivity of allylboration of 4-formyl[2.2]paracyclophane, 4-acetyl[2.2]paracyclophane, and 4-hydroxy-5-formyl[2.2]paracyclophane was studied and the relative configurations of the homoallylic alcohols obtained were established. Optically pure (Sp,Sc)-(+)-4-(4-hydroxy-1-methylbut-3-enyl)[2.2]paracyclophane and (Rc,Sc)-(+)-4-hydroxy-5-(4-hydroxybut-3-enyl)[2.2]paracyclophane were synthesized. The possibility of using (Sp,Sc)-(+)-4-(4-hydroxy-4-methylbut-3-enyl)[2.2]paracyclophane as a recoverable chiral auxiliary in asymmetric allylboration of aldehydes was demonstrated. Kluwer Academic/Plenum Publishers, 2000 [2.2]paracyclophane nationallicence allylboration nationallicence stereoselectivity nationallicence optical activity nationallicence carbonyl derivatives nationallicence homoallylic alcohols nationallicence chiral auxiliaries of asymmetric synthesis nationallicence Vorontsova N. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut Rozenberg V. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut Vorontsov E. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut Tok O. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut Bubnov Yu A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/5(2000-05-01), 912-919 1066-5285 49:5<912 2000 49 11172 https://doi.org/10.1007/BF02494718 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02494718 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Vorontsova N. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Rozenberg V. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Vorontsov E. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Tok O. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Bubnov Yu A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut NATIONALLICENCE 773 0- Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/5(2000-05-01), 912-919 1066-5285 49:5<912 2000 49 11172 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer