Controllable Access to Diazo-functionalized 2-Methylene-2,3-dihydrofurans and Diazo-functionalized Furans from Enynones and Diazo Carbonyl Compounds.

Using enynones and diazo carbonyl compounds as identical starting materials, methods for chemoselective and regioselective constructs of diazo-functionalized 2-methylene-2,3-dihydrofurans and diazo-functionalized trisubstituted furans have been established in a AgSbF 6 /DBU/DCE/0 °C system and a AgSbF 6 /DBU/Et 2 O·BF 3 /DCE/0 °C system, respectively. A Lewis acid and organic base cocontrolled reaction for the synthesis of diazo-functionalized trisubstituted furans is infrequent. For diazo-functionalized 2-methylene-2,3-dihydrofuran synthesis, the reaction possesses excellent diastereoselectivity and Z -selectivity. On the basis of Rh 2 (OAc) 4 -mediated unique decomposition of diazo-functionalized 2-methylene-2,3-dihydrofurans, an application to diastereoselective construction of a 5-methylene-4,7-dihydro-5 H -furo[2,3- c ]pyran frame has been achieved for the first time.