Organozinc halides derived from Grignard reagents behave differently in their reaction with ethyl (±)-(2RS,3SR)-tetrahydro-4-methylene-2-phenyl-3- (phenylsulfonyl)furan-3-carboxylate (3) according to the hybridisation of the carbon ligand. During the development of short multi-component reactions for the synthesis of diverse functionalized ethyl 2,5-dihydrofuran-3-carboxylates it was discovered that aryl and vinyl zinc halides undergo clean reaction with 3 in the presence of Pd(PPh3)4. In contrast, when alkyl zinc halides are reacted with 3 in the presence of Pd(PPh3)4, reductive desulfonation of 3 is observed. Remarkably, in the absence of a transition metal catalyst, the allylic substitution of 3 with alkyl zinc halides proceeds cleanly and in moderate to good yield.
|Original language||English (US)|
|Number of pages||8|
|Journal||European Journal of Organic Chemistry|
|State||Published - May 1 2000|
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry