Cobalt cluster-containing carbonyl ylides for catalytic, three-component assembly of oxygen heterocycles.
[reaction: see text] A dicobalt hexacarbonyl (Co(2)(CO)(6)) cluster is essential for the unusually broad dipolarophile scope and for the sense and degree of diastereoselection in a catalytic, three-component synthesis of tetrahydrofurans and dihydrofurans. Likely involving a new class of carbonyl ylide, these cycloadditions are stereospecific with respect to the dipolarophile and exhibit high diastereoselectivity and regioselectivity in most cases. Differentiation of all four positions of the tetrahydrofuran can thus be accomplished in a triply convergent manner.
Skaggs
Aaron J
AJ
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, Massachusetts 02139, USA.
Lin
Eleanor Y
EY
Jamison
Timothy F
TF
D001685:Biological Factors / Q000138:chemical synthesis; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D013237:Stereoisomerism
D001685:Biological Factors; D005663:Furans; D006571:Heterocyclic Compounds; D009942:Organometallic Compounds; D003035:Cobalt; C018674:tetrahydrofuran; D010100:Oxygen