TY - JOUR
T1 - Significant counterion effect of the In(III)-pybox complex in highly enantioselective carbonyl-ene reactions of ethyl glyoxylate
AU - Zhao, Jun Feng
AU - Tjan, Teguh Budiono W.
AU - Loh, Teck Peng
PY - 2010/10/2
Y1 - 2010/10/2
N2 - A highly efficient enantioselective carbonyl-ene reaction of ethyl glyoxylate catalyzed by an In(III)-pybox complex, which is designed based on the counterion effect, is reported. Reactions of both aliphatic and aromatic 1,1-disubstituted olefins proceed smoothly to give enantioenriched homoallylic alcohols with excellent yields and enantioselectivities. In addition, electron-withdrawing as well as donating groups on the phenyl ring of α-methyl styrenes are tolerated in this reaction.
AB - A highly efficient enantioselective carbonyl-ene reaction of ethyl glyoxylate catalyzed by an In(III)-pybox complex, which is designed based on the counterion effect, is reported. Reactions of both aliphatic and aromatic 1,1-disubstituted olefins proceed smoothly to give enantioenriched homoallylic alcohols with excellent yields and enantioselectivities. In addition, electron-withdrawing as well as donating groups on the phenyl ring of α-methyl styrenes are tolerated in this reaction.
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U2 - 10.1016/j.tetlet.2010.06.066
DO - 10.1016/j.tetlet.2010.06.066
M3 - Article
AN - SCOPUS:77957112412
SN - 0040-4039
VL - 51
SP - 5649
EP - 5652
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 43
ER -