Year: 2008
Type: editorial
Abstract: Significance The synthesis of cis -2,5-disubstituted tetrahydrofurans via Lewis acid catalyzed [3+2] cycloaddition of cyclopropanes with aldehydes is described. Treatment of racemic 2-aryl-cyclopropanes 1 with a range of aldehydes 2 using Sn(OTf) 2 as catalyst led to cis -substituted tetrahydrofurans 3 in good to excellent yield, with excellent diastereoselectivity in most cases. Extensive screening of Lewis acids was carried out to obtain the optimized conditions. A broad range of functional groups are tolerated and optically active tetrahydrofurans 6 may be obtained from enantiopure cyclopropane 4 without the need for a chiral ligand control. Inversion of the stereocenter was observed during this process. The scope of the reaction was extended to accommodate the reaction of vinylcyclopropanes 7 with both aldehydes and ketones 8 to give tetrahydrofurans 9 , also in high yield and diastereoselectivity.
Source: Synfacts
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W2085391079