The discovery and synthetic applications of a widely applicable and highly enantioselective (&gt;99% ee) protocol consisting of the ZACA reaction (Zr-catalyzed asymmetric carboalumination of alkenes), purification of the ZACA-products by lipase-catalyzed acetylation, and subsequent transformations, such as Pd-, Ni-, or Cu-catalyzed cross-coupling are discussed.<br/><br/>In contrast with the Sharpless epoxidation, the Noyori hydrogenation, both of which require allylic OH substituent for satisfactory asymmetric transformations, the ZACA – Lipase-catalyzed acetylation – Cross-coupling protocol in principle requires only terminal alkenes. In practice, however, the presence of a proximal hetero-functional group can be tolerated for converting terminal alkene into a wide range of chiral organic compounds including even those displaying very feeble optical rotations, such as isotopomers, as highly pure compounds of 99.9% ee or even higher!

On the magical power of d-block transition metals as exemplified by ZACA (Zr-catalyzed asymmetric carboalumination of alkenes) – lipase-catalyzed acetylation – transition metal-catalyzed cross-coupling for highly enantioselective synthesis of various types of chiral organic compounds

249th National Meeting (2015)

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