The chiral 1,3-dimethyl moieties (deoxypropionates) and 1,5-dimethyl moieties (isoprenoids) are widely found in numerous natural products and bioactive compounds so that substantial efforts have been made to develop synthetic methods for the stereoselective construction of deoxypropionates and isoprenoids. A large variety of the synthetic approaches have been reported to date, and the approaches enabled the preparation of corresponding deoxypropionates and isoprenoids. However, the majority of reported methods have to install temporary directing groups or chiral auxiliaries to assist asymmetric C–C bond or C–H bond formation that are to be removed later. Thus, these methods experienced some drawbacks including long synthetic sequences, the use of stoichiometric quantities of chiral reagents, and/or low stereoselectivity. Herein, we would like to present our recent progress on the development of highly enantioselective (&gt;99% ee) and catalytic routes to a wide range of deoxypropionates and isoprenoids through the combination of ZACA reaction (Zirconium-catalyzed asymmetric carboalumination of alkenes) and transition metal-catalyzed cross-coupling reactions, which is a highly reliable and predictable method for the preparation of both enantiomerically and diastereomerically pure deoxypropionates and isoprenoids.

Highly efficient and enantioselective synthesis of deoxypropionates and isoprenoids

253rd National Meeting (2017)

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