ASYMMETRIC-SYNTHESIS OF 2,3-DIHYDROFURANS BY REACTION OF RHODIUM-STABILIZED VINYLCARBENOIDS WITH VINYL ETHERS

Authors
DAVIES HML AHMED G CALVO RL CHURCHILL MR CHURCHILL DG
Citation
Hml. Davies et al., ASYMMETRIC-SYNTHESIS OF 2,3-DIHYDROFURANS BY REACTION OF RHODIUM-STABILIZED VINYLCARBENOIDS WITH VINYL ETHERS, Journal of organic chemistry, 63(8), 1998, pp. 2641-2645
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
8
Year of publication
1998
Pages
2641 - 2645
Database
ISI
SICI code
0022-3263(1998)63:8<2641:AO2BRO>2.0.ZU;2-0
Abstract
Rhodium(II) octanoate catalyzed decomposition of 2-diazo-3-siloxybuten oates, containing (R)-pantolactone as a chiral auxiliary, in the prese nce of vinyl ethers results in the diastereoselective synthesis of cyc lopropanes with high asymmetric induction. Treatment of the cyclopropa nes with tetrabutylammonium fluoride results in desilylation and ring expansion of the resulting acylcyclopropanes to 2,3-dihydrofurans with retention of stereochemistry.