TY - JOUR
T1 - Enantioselective intramolecular [2 + 2 + 2] cycloaddition of enediynes for the synthesis of chiral cyclohexa-1,3-dienes
AU - Shibata, Takanori
AU - Kurokawa, Hiroshi
AU - Kanda, Kazumasa
PY - 2007/8/17
Y1 - 2007/8/17
N2 - (Chemical Equation Presented) The enantioselective intramolecular [2 + 2 + 2] cycloaddition of various enediynes, where two acetylenic moieties are connected by a trans-olefinic moiety, gave chiral tricyclic cyclohexa-1,3-dienes using Rh-H8-BINAP catalyst. In the case of carbon-atom-tethered enediynes, enantioselectivity was generally good-to-high regardless of the substituents on their alkyne termini. In contrast, with heteroatom-tethered enediynes, appropriate substituents were required to induce the oxidative coupling of alkyne and alkene moieties before that of two alkyne moieties, which would be important for highly enantioselective intramolecular cycloaddition.
AB - (Chemical Equation Presented) The enantioselective intramolecular [2 + 2 + 2] cycloaddition of various enediynes, where two acetylenic moieties are connected by a trans-olefinic moiety, gave chiral tricyclic cyclohexa-1,3-dienes using Rh-H8-BINAP catalyst. In the case of carbon-atom-tethered enediynes, enantioselectivity was generally good-to-high regardless of the substituents on their alkyne termini. In contrast, with heteroatom-tethered enediynes, appropriate substituents were required to induce the oxidative coupling of alkyne and alkene moieties before that of two alkyne moieties, which would be important for highly enantioselective intramolecular cycloaddition.
UR - http://www.scopus.com/inward/record.url?scp=34547938721&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=34547938721&partnerID=8YFLogxK
U2 - 10.1021/jo070762d
DO - 10.1021/jo070762d
M3 - Article
C2 - 17636959
AN - SCOPUS:34547938721
SN - 0022-3263
VL - 72
SP - 6521
EP - 6525
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 17
ER -