Abstract
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 AgSbF6/DBU/DCE/0 °C system and a AgSbF6/DBU/Et2O·BF3/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 Rh2(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-5H-furo[2,3-c]pyran frame has been achieved for the first time.
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