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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
Published on: February 15, 2016
Stereoselectivity in trimethylenemethane (TMM) diyl mediated cycloaddition reaction to angularly fused triquinanes
Yeokwon Yoon1, Taek Kang, Hee-Yoon Lee
1Department of Chemistry, KAIST, 373-1 Gusung Dong, Yuseong, Daejeon, 305-701, Korea.
Abstract:
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.
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