Inter- and intramolecular [4 + 3] cycloadditions using epoxy enol silanes as functionalized oxyallyl cation precursors.
Using epoxy enol triethylsilanes as oxyallyl cation precursors, [4 + 3] cycloadditions with various dienes occur under catalysis by silyl triflates and acids in good yields. The intramolecular [4 + 3] cycloaddition proceeds under mild conditions and generate hydroxylated cycloadducts with high diastereoselectivity and yields. Enantiomerically pure epoxy enol silanes have been shown to give excellent yields of the optically pure cycloadduct bearing multiple stereocenters.
Chung
Wing Ki
WK
Department of Chemistry and the Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, PR China.
Lam
Sze Kui
SK
Lo
Brian
B
Liu
Lok Lok
LL
Wong
Wing-Tak
WT
Chiu
Pauline
P
D000143:Acids / Q000737:chemistry*; D000466:Alkadienes / Q000138:chemical synthesis / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D002412:Cations / Q000737:chemistry*; D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D012821:Silanes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000143:Acids; D000466:Alkadienes; D001643:Bridged Bicyclo Compounds; D002412:Cations; D004852:Epoxy Compounds; D017646:Organosilicon Compounds; D012821:Silanes; C541595:epoxy enol triethylsilane