Ei-ichi Negishi (2015) - How to Synthesize a Wide Variety of Optically Active Organic and Bioorganic Compounds of >99% Optical Purity

Ei-ichi Negishi (2015)

How to Synthesize a Wide Variety of Optically Active Organic and Bioorganic Compounds of >99% Optical Purity

Ei-ichi Negishi (2015)

How to Synthesize a Wide Variety of Optically Active Organic and Bioorganic Compounds of >99% Optical Purity

Abstract

The discovery and synthetic applications of a widely applicable and highly enantioselective (>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- or Cu-catalyzed cross-coupling are discussed.

In contrast with many other methods for asymmetric transformations requiring directing groups in the substrates, the ZACA–Lipase-catalyzed acetylation–Transition metal-catalyzed cross-coupling protocol in principle requires only simple alkenes. In practice, however, the presence of a proximal hetero-functional group can be tolerated for converting terminal alkenes 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% ee or even higher. We now believe that one of the last bastions in organic synthesis may have been conquered.

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