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Copper‐Catalyzed Asymmetric Allylic Alkylation of Racemic Cyclic Substrates: Application of Dynamic Kinetic Asymmetric Transformation (DYKAT)
Author(s) -
Langlois JeanBaptiste,
Alexakis Alexandre
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900790
Subject(s) - chemistry , kinetic resolution , tsuji–trost reaction , reagent , allylic rearrangement , catalysis , alkylation , copper , combinatorial chemistry , organic chemistry , enantioselective synthesis
The copper‐catalyzed asymmetric allylic alkylation (AAA) is of great interest in organic synthesis. This reaction was extensively studied using a broad range of substrates, ligands and organometallic reagents. However, the use of racemic substrates was still limited. Although some processes of kinetic resolution are reported in the literature, no examples of quantitative deracemization are described as is the case for the Pd‐catalyzed allylic alkylation. We present here a full account of our investigations through the development of the first example of such a process in copper‐catalyzed AAA. High enantioselectivities (up to 99% ee ), scope of the reaction and mechanistic considerations are reported herein.