Dynamic kinetic asymmetric transformation (DYKAT) by combined amine- and transition-metal-catalyzed enantioselective cycloisomerization.
The first examples of one-pot highly chemo- and enantioselective dynamic kinetic asymmetric transformations (DYKATs) involving alpha,beta-unsaturated aldehydes and propargylated carbon acids are presented. These DYKATs, which proceed by a combination of catalytic iminium activation, enamine activation, and Pd(0)-catalyzed enyne cycloisomerization, give access to functionalized cyclopentenes with up to 99 % ee and can be used for the generation of all-carbon quaternary stereocenters.
Zhao
Gui-Ling
GL
Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden.
Ullah
Farman
F
Deiana
Luca
L
Lin
Shuangzheng
S
Zhang
Qiong
Q
Sun
Junliang
J
Ibrahem
Ismail
I
Dziedzic
Pawel
P
Córdova
Armando
A
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D056004:Molecular Dynamics Simulation; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D028561:Transition Elements / Q000138:chemical synthesis* / Q000737:chemistry
D000588:Amines; D003517:Cyclopentanes; D028561:Transition Elements; D010165:Palladium