Proline-Related Secondary Amine Catalysts and Applications

Proline-Related Secondary Amine Catalysts and Applications 

In this chapter we will deal with organocatalytic asymmetric transformations using these catalysts, mainly focusing on the significant and major achievements in this area published from 2000 to 2011. However, due to space constraints, this chapter will not cover the great utiHty of diarylprolinol catalysts (category F) for convenience, only references are given [3]. 

Comprehensive Enantioselective Organocatalysis Catalysts, Reactions, and Applications, First Edition. 

In this context, prolinamide 2 [5-8] and its aryl-substituted homologs such as 3-5 have been developed [9-14]. Analogous to these examples, binaphthyldiamine-derived compounds such as 6 and 7 have been introduced for use in aqueous systems and as recoverable catalysts [15-18]. For example, Benaglia and coworkers reported that the prolinamide catalyst 7 with a UpophiUc side chain showed efficient catalytic activity in water [16b]. Chiral spiro diamine-derived catalysts have also been designed, albeit in moderate enantioselectivity [19]. Owing to the increased acidity of an NH group of thioamide relative to a normal amide, proline-thioamide catalysts such as 8 have been shown to be more effective [20-23]. 

Several other related systems containing a prolinamide or proline-thioamide core have also been reported [36—42]. 

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J Proline-Related Secondary Amine Catalysts and Applications... 

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