TY - JOUR
T1 - Diastereoselectivity studies on the photo-activated cycloaddition of 5-(1,2-dioxyethyl)-2(5H)-furanones to alkenes
AU - Cucarull-González, Joan R.
AU - Alibés, Ramon
AU - Figueredo, Marta
AU - Font, Josep
PY - 2015/1/29
Y1 - 2015/1/29
N2 - ©ARKAT-USA, Inc. A series of 2(5H)-furanones, bearing a 1,2-dioxyethyl substituent at the γ-carbonyl position, have been prepared and explored as substrates in photochemical reactions with alkenes. Compared to the simpler oxymethyl analogues, the homologation of the side chain is highly beneficial to the antifacial selectivity of the [2+2] cycloadditions. Most reactions occur in synthetically useful yields, giving access to new polyfunctionalized cyclobutane-fused furanones.
AB - ©ARKAT-USA, Inc. A series of 2(5H)-furanones, bearing a 1,2-dioxyethyl substituent at the γ-carbonyl position, have been prepared and explored as substrates in photochemical reactions with alkenes. Compared to the simpler oxymethyl analogues, the homologation of the side chain is highly beneficial to the antifacial selectivity of the [2+2] cycloadditions. Most reactions occur in synthetically useful yields, giving access to new polyfunctionalized cyclobutane-fused furanones.
KW - Diastereoselectivity
KW - Furanones
KW - Photochemistry
KW - [2+2] cycloaddition
U2 - 10.3998/ark.5550190.0016.314
DO - 10.3998/ark.5550190.0016.314
M3 - Article
SN - 1551-7004
VL - 2015
SP - 193
EP - 213
JO - Arkivoc
JF - Arkivoc
IS - 3
ER -