A three-component coupling strategy for tetrahydrofuran synthesis: application of the diisopropyl tartrate modified (E)-gamma-(dimethylphenylsilyl)allylboronate as an alpha,gamma-allyl dianion equivalent.
[reaction: see text] A highly convergent three-component coupling strategy for the stereocontrolled synthesis of 2,3,5-trisubstituted tetrahydrofurans is described. After allylboration of the first aldehyde with 1, the chiral, nonracemic allylsilanes 2 are coupled with a second aldehyde or ketone with Lewis acid catalysis to give tetrahydrofurans 3 or 4 with excellent selectivity. The 2,5-stereochemistry is controlled by operating under nonchelate (e.g., 3) or chelate (e.g., 4) conditions.
Micalizio
G C
GC
Department of Chemistry, University of Michigan, Ann Arbor 48109, USA.
Roush
W R
WR
D000498:Allyl Compounds / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis*; D017646:Organosilicon Compounds / Q000737:chemistry*
D000498:Allyl Compounds; D001897:Boronic Acids; D005663:Furans; D017646:Organosilicon Compounds; C408886:diisopropyl 2-bora-2-(3-(phenyldimethylsilyl)-2-propen-1-yl)-1,3-dioxole-4,5-dicarboxylate; C018674:tetrahydrofuran