Controllable Access to Diazo-functionalized 2-Methylene-2,3-dihydrofurans and Diazo-functionalized Furans from Enynones and Diazo Carbonyl Compounds
JOURNAL OF ORGANIC CHEMISTRY(2023)
摘要
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 degrees C system and a AgSbF6/DBU/Et2OBF3/DCE/0 degrees 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-5H-furo[2,3-c]pyran frame has been achieved for the first time.
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