TY - JOUR
T1 - Enantioselective intramolecular [2 + 2 + 2] cycloaddition of 1,4-diene-ynes
T2 - A new approach to the construction of quaternary carbon stereocenters
AU - Shibata, Takanori
AU - Tahara, Yu Ki
PY - 2006/9/13
Y1 - 2006/9/13
N2 - The intramolecular [2 + 2 + 2] cycloaddition of various 1,4-diene-ynes was examined using a chiral rhodium catalyst. In the case of 1,4-diene-ynes with a substituent at the 2-position of the 1,4-diene moiety, tricyclic compounds possessing a strained bicyclo[2.2.1]heptene skeleton with two quaternary carbon stereocenters were obtained in high enantiomeric excess. On the other hand, in the case of 1,4-diene-ynes with no substituent at this position, bicyclic cyclohexa-1,3-dienes with a quaternary carbon stereocenter were obtained probably by carbon-carbon bond cleavage of the reaction intermediate.
AB - The intramolecular [2 + 2 + 2] cycloaddition of various 1,4-diene-ynes was examined using a chiral rhodium catalyst. In the case of 1,4-diene-ynes with a substituent at the 2-position of the 1,4-diene moiety, tricyclic compounds possessing a strained bicyclo[2.2.1]heptene skeleton with two quaternary carbon stereocenters were obtained in high enantiomeric excess. On the other hand, in the case of 1,4-diene-ynes with no substituent at this position, bicyclic cyclohexa-1,3-dienes with a quaternary carbon stereocenter were obtained probably by carbon-carbon bond cleavage of the reaction intermediate.
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U2 - 10.1021/ja0639160
DO - 10.1021/ja0639160
M3 - Article
C2 - 16953610
AN - SCOPUS:33748481111
SN - 0002-7863
VL - 128
SP - 11766
EP - 11767
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 36
ER -