000204019 001__ 204019
000204019 005__ 20180913062908.0
000204019 0247_ $$2doi$$a10.1002/anie.201408364
000204019 022__ $$a1433-7851
000204019 02470 $$2ISI$$a000345317000044
000204019 037__ $$aARTICLE
000204019 245__ $$aNickel(0)-Catalyzed Enantioselective Annulations of Alkynes and Arylenoates Enabled by a Chiral NHC Ligand: Efficient Access to Cyclopentenones
000204019 260__ $$aWeinheim$$bWiley-Blackwell$$c2014
000204019 269__ $$a2014
000204019 300__ $$a5
000204019 336__ $$aJournal Articles
000204019 520__ $$aCyclopentenones are versatile structural motifs of natural products as well as reactive synthetic intermediates. The nickel-catalyzed reductive [3+2] cycloaddition of alpha,beta-unsaturated aromatic esters and alkynes constitutes an efficient method for their synthesis. Here, nickel(0) catalysts comprising a chiral bulky C-1-symmetric N-heterocyclic carbene ligand were shown to enable an efficient asymmetric synthesis of cyclopentenones from mesityl enoates and internal alkynes under mild conditions. The bulky NHC ligand provided the cyclopentenone products in very high enantioselectivity and led to a regioselective incorporation of unsymmetrically substituted alkynes.
000204019 6531_ $$aannulation
000204019 6531_ $$aasymmetric catalysis
000204019 6531_ $$acarbenes
000204019 6531_ $$acyclopentenones
000204019 6531_ $$anickel
000204019 700__ $$0246120$$aAhlin, Joachim S. E.$$g221028
000204019 700__ $$0245585$$aDonets, Pavel A.$$g213431
000204019 700__ $$0244709$$aCramer, Nicolai$$g206338
000204019 773__ $$j53$$k48$$q13229-13233$$tAngewandte Chemie-International Edition
000204019 909C0 $$0252404$$pLCSA$$xU12340
000204019 909CO $$ooai:infoscience.tind.io:204019$$pSB$$particle
000204019 917Z8 $$x206338
000204019 937__ $$aEPFL-ARTICLE-204019
000204019 973__ $$aEPFL$$rREVIEWED$$sPUBLISHED
000204019 980__ $$aARTICLE