Iodine(III)-promoted ring expansion of 1-vinylcycloalkanol derivatives: a metal-free approach toward seven-membered rings.
A versatile and metal-free approach for the synthesis of molecules bearing seven- and eight-membered rings is described. The strategy is based on the ring expansion of 1-vinylcycloalkanols (or the corresponding silyl or methyl ether) mediated by the hypervalent iodine reagent HTIB (PhI(OH)OTs). The reaction condition can be easily adjusted to give seven-membered rings bearing different functional groups. A route to medium-ring lactones was also developed.
Silva
Luiz F
LF
Instituto de Química, Universidade de São Paulo, Avenida Professor Lineu Prestes, 748, CP 26077, CEP 05513-970 São Paulo SP, Brazil. luizfsjr@iq.usp.br
Vasconcelos
Ramon S
RS
Nogueira
Mário A
MA
D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D003516:Cycloparaffins / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry*
D003516:Cycloparaffins; D011084:Polycyclic Aromatic Hydrocarbons; D014753:Vinyl Compounds; D007455:Iodine