Trans-2,5-disubstituted tetrahydrofurans via addition of carbon nucleophiles to the strained bicyclic acetal 2,7-dioxabicyclo[2.2.1]heptane.
Addition of allyltributylstannane to 2,7-dioxabicyclo[2.2.1]heptane in the presence of TiCl(4) produces 5-allyl-2-(hydroxymethyl)tetrahydrofuran with a trans/cis ratio of 93:7. The trans-selectivity is also observed in additions of various other carbon nucleophiles.
Friestad
Gregory K
GK
Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA. gregory-friestad@uiowa.edu
Lee
Hye Jin
HJ
D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006536:Heptanes / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D017971:Tin Compounds / Q000737:chemistry
D001643:Bridged Bicyclo Compounds; D005663:Furans; D006536:Heptanes; D017971:Tin Compounds; C023599:stannous chloride