Optically active angularly condensed [2.2]paracyclophanes containing five-membered rings have been synthesized by a two-step approach based on the Diels-Alder cycloaddition of (S)-(+)-4-vinyl[2.2]paracyclophane. Structural analysis by NMR spectroscopy is presented. These helicenophanes containing a cyclopentane ring show extraordinarily high specific rotations. This phenomenon has been discussed in terms of structural modifications caused by the replacement of the benzene unit with a cyclopentane ring. © 2003 Elsevier Science Ltd. All rights reserved.
Synthesis of enantiopure angularly condensed [2.2]paracyclophanes containing five-membered rings / Lucio, Minuti; Aldo, Taticchi; Assunta, Marrocchi; Daniela, Lanari; Broggi, Alessandra; Eszter Gacs, Baitz. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 14:4(2003), pp. 481-487. [10.1016/s0957-4166(02)00833-9]
Synthesis of enantiopure angularly condensed [2.2]paracyclophanes containing five-membered rings
BROGGI, ALESSANDRA;
2003
Abstract
Optically active angularly condensed [2.2]paracyclophanes containing five-membered rings have been synthesized by a two-step approach based on the Diels-Alder cycloaddition of (S)-(+)-4-vinyl[2.2]paracyclophane. Structural analysis by NMR spectroscopy is presented. These helicenophanes containing a cyclopentane ring show extraordinarily high specific rotations. This phenomenon has been discussed in terms of structural modifications caused by the replacement of the benzene unit with a cyclopentane ring. © 2003 Elsevier Science Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
