TY - JOUR T1 - Enantioselective intramolecular [2 + 2 + 2] cycloaddition of 1,4-diene-ynes: a new approach to the construction of quaternary carbon stereocenters. AU - Shibata,Takanori, AU - Tahara,Yu-ki, PY - 2006/9/7/pubmed PY - 2006/9/7/medline PY - 2006/9/7/entrez SP - 11766 EP - 7 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 128 IS - 36 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. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/16953610/Enantioselective_intramolecular_[2_+_2_+_2]_cycloaddition_of_14_diene_ynes:_a_new_approach_to_the_construction_of_quaternary_carbon_stereocenters_ L2 - https://doi.org/10.1021/ja0639160 DB - PRIME DP - Unbound Medicine ER -