264255-80-3Relevant articles and documents
Formation of medium-size bridged ring systems via ring-closing metathesis of 2,5-disubstituted-2,3-dihydro-1H-pyrroles
Bamford, Samantha J.,Goubitz, Kees,Van Lingen, Hester L.,Luker, Tim,Schenk, Henk,Hiemstra, Henk
, p. 345 - 351 (2000)
A series of 2,5-disubstituted-2,3-dihydro-1H-pyrroles were prepared via diastereoselective alkylations of sulfone 10. Ring-closing metathesis (RCM), using Grubbs catalyst, provided bridged ring systems with newly formed 9-to 12-membered rings in moderate to good yields. The 9-membered ring was formed as a single Z-isomer whereas the 10- to 12-membered rings were formed as mixtures of E- and Z-isomers. It was shown that the minor diastereomer obtained from the alkylation product 11c failed to undergo RCM, illustrating the crucial aspect of substrate conformation.