133620-89-0Relevant academic research and scientific papers
REARRANGEMENT OF EPOXIDIZED BENZYNE/FURAN CYCLOADDUCTS: A CONVENIENT ROUTE TO α-FORMYL AND α-ACYL-2-INDANONES
French, Larry G.,Fenlon, Edward E.,Charlton, Timothy P.
, p. 851 - 854 (1991)
The Lewis acids, LiClO4 and BF3*Et2O, promote carbocation driven ring contracting rearrangements of epoxides derived from the Diels-Alder adducts of benzyne and furans.This unprecedented transformation provides moderate to excellent yields of novel α-formyl and α-acyl-2-indanones.
Enantioselective alkylative double ring-opening of epoxides derived from cyclic allylic ethers: Synthesis of enantioenriched unsaturated diols
Hodgson, David M.,Stent, Matthew A.H.,Stefane, Bogdan,Wilson, Francis X.
, p. 1139 - 1150 (2003)
A screen of external chiral ligands has led to enantioselective organolithium-induced alkylative double ring-opening of 3,4-epoxytetrahydrofuran 1 with n-BuLi to give 3-methyleneheptane-1,2-diol 3 in 75% yield and 55% ee in the presence of bisoxazoline 10, and in up to 60% ee in the presence of ( - )-sparteine 2. Extending the alkylative double ring-opening reaction to epoxides derived from oxabicyclo[n.2.1]alkenes (n = 2, 3) results in the formation of cycloalkenediols, which, when carried out in the presence of ( - )-sparteine 2 affords products in up to 85% ee.
