Synthesis of chiral nitrogen heterocycles from carbohydrates, amines and organoboron compounds

ORGN 771

Nicos A. Petasis, petasis@usc.edu and Alexey N. Butkevich. Department of Chemistry and Loker Hydrocarbon Research Institute, University of Southern California, Los Angeles, CA 90089-1661
The synthesis of 5- and 6-membered N-heterocycles in enantiomerically pure form is of great ongoing interest, particularly for the synthesis of bioactive natural products and for many medicinal chemistry applications. Although many strategies are available for the preparation of such compounds, there is still a need to develop new and practical methods for the synthesis of these molecules, particularly those with high molecular complexity. Herein, we present a new approach towards a number of N-heterocycles that relies on the one-step three-component reaction of carbohydrates, amines and organoboron compounds. In particular we will present a concise approach to both enantiomeric forms of substituted isoindoline derivatives. This strategy is highly versatile and allows the synthesis of many types of novel molecules from readily available starting materials. The scope and limitations of this methodology, along with further transformations of the products, will be presented.