Stereoselectivity in trimethylenemethane (TMM) diyl mediated cycloaddition reaction to angularly fused triquinanes.
A thorough study on the diastereoselectivity in the TMM diyl mediated [2+3] cycloaddition reaction of monosubstituted linear substrates to form angularly fused triquinanes was carried out. Substitution at position 3 provided complete diastereoselectivity, while positions 1 and 4 induced marginal stereoselectivity. Position 2 did not show any influence on the diastereoselectivity. Position 4 turned out to be incompatible with the cycloaddition reaction as the carbene intermediate underwent O-Si bond insertion to form a dihydrofuran ring.
Department of Chemistry, KAIST, 373-1 Gusung Dong, Yuseong, Daejeon, 305-701, Korea.
Yeokwon
Y
Yoon
Taek
T
Kang
Hee-Yoon
HY
Lee