Heterogeneous enantioselective catalysts: strategies for the immobilisation of homogeneous catalysts

• Published in: Chemical Society reviews 2004-02, Vol.33 (2), p.108-122
• Main Authors: McMorn, Paul, Hutchings, Graham J
• Format: Article
• Language: English
• Subjects: Adsorption; Catalysis; Chemistry, Organic - methods; Enzymes, Immobilized; Models, Chemical; Molecular Structure; Organic Chemicals - chemistry; Organometallic Compounds - chemistry; Silicon Dioxide - chemistry; Zeolites - chemistry
• ISSN: 0306-0012; 1460-4744
• DOI: 10.1039/b200387m

Enantioselective formation of C-H, C-C, C-O and C-N bonds has been extensively studied using homogeneous asymmetric catalysts for many years. However, these catalysts have yet to make a significant impact in the industrial synthesis of fine chemicals. A central reason is that homogeneous asymmetric catalyst design requires relatively bulky ligands and catalyst re-use through recovery and recycle often causes problems. One mechanism to overcome this problem is to immobilise the asymmetric catalyst onto a support and the resulting heterogeneous asymmetric catalyst can, in principle, be readily re-used. This tutorial review covers the different methodologies for immobilisation, including: adsorption, encapsulation, tethering using a covalent bond and electrostatic interaction and is aimed at both researchers new to the field and those with a wider interest in the immobilisation of homogeneous catalysts. Most importantly, recent studies will be highlighted that demonstrate that immobilised catalysts can give higher enantioselection when compared with their non-immobilised counterparts and the question of how high enantioselection can be achieved is addressed.