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Synthesis 2014; 46(10): 1303-1310
DOI: 10.1055/s-0033-1340883
DOI: 10.1055/s-0033-1340883
special topic
Efficient and Highly Enantioselective Aerobic Oxidation–Michael–Carbocyclization Cascade Transformations by Integrated Pd(0)-CPG Nanoparticle/Chiral Amine Relay Catalysis
Further Information
Publication History
Received: 08 January 2014
Accepted: 08 February 2014
Publication Date:
17 March 2014 (online)
Abstract
A series of highly diastereo- and enantioselective aerobic oxidation–Michael–carbocyclization cascade transformations by integrated heterogeneous Pd(0)-CPG nanoparticle/chiral amine relay catalysis are disclosed. The heterogeneous Pd(0)-CPG nanoparticle catalysts were efficient for both the sequential aerobic oxidation and dynamic kinetic asymmetric Michael–carbocyclization transformations, resulting in 1) oxidation of a variety of allylic alcohols to enals and 2) formation of cyclopentenes containing an all-carbon quaternary stereocenter in good to high yields with up to 20:1 dr and 99.5:0.5 er.
Key words
asymmetric cocatalysis - aerobic oxidations - relay catalysis - integrated heterogeneous catalysis - integrated homogeneous catalysis - quaternary stereocentersSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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For selected examples, see:
This technique has also been used for immobilization of Ru, see: