Asymmetric Syntheses Utilizing Nitroolefins.

Abstract

Nitroolefins are versatile synthetic intermediates in organic synthesis because of excellent ability for carbon-carbon bond formation and easy transformation to a variety of functional groups. In the reaction of enolates with chiral nitroolefins, a chiral hetero substituent is replaced by the carbon substituents via addition-elimination process. The scope, limitations, and the mechanism for this type of asymmetric induction will be discussed. The resulting chiral nitroolefins have a wide utility as chiral building blocks for the chiral syntheses of the natural products, such as Aspidosperma, Hunteria, and Physostigma alkaloids, tricyclic diterpenoids and sesquiterpenoids.