Synthese optisch aktiver Olefin-Bausteine aus D-Ribonolacton: Isopropyliden-Derivate von D-erythro-Pentendi- und -triolen (cis-4-substituierte 5-Vinyldioxolane)

Abstract

Synthesis of Optically Active Olefinic Building Blocks from D-Ribonolactone: Isopropylidene Derivatives of D-erythro-Pentenediol and -triol (cis-4-Substituted 5-Vinyldioxolanes) Optically active D-erythro-pentenediol and -triol acetonides 4-11 were prepared from D-ribonolactone 1, via the acid 4 and the alcohol 9 as key intermediates. Acetonides 4-11 are cis-4-substituted 5-vinyldioxolanes, both needed as standard model substrates for studies of asymmetric induction in (cyclo)additions to α-chiral olefins and as versatile synthetic building blocks. The acid-catalyzed rearrangement of an internal acetonide (9) to the terminal isomer (13) is demonstrated.