Isomerization-cyclization approach to the synthesis of 2-hydroxy-5-alkylidene-cyclopent-2-enones.
[reaction: see text]. Propargyl vinyl ketones that are derived from the addition of 1-lithio-1-methoxymethoxy-2-ynes to morpholino enamides undergo isomerization followed by cyclization to alpha-methylene cyclopentenones upon exposure to silica gel.
Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, Hawaii 96822, USA.
Jeremy
J
Forest
Cisco
C
Bee
Frank
F
Cordaro
Marcus A
MA
Tius
D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry; D007536:Isomerism; D015394:Molecular Structure; D058428:Silica Gel; D012822:Silicon Dioxide / Q000737:chemistry
D003517:Cyclopentanes; D004987:Ethers; D058428:Silica Gel; D012822:Silicon Dioxide; C013905:cyclopentenone