Developing an Understanding of Asymmetric Induction

University Of Pennsylvania, Philadelphia PA

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Abstract

DESCRIPTION (provided by applicant): The broad, long-term objectives of this proposal are to develop new synthetic methods that enable the preparation of important intermediates for organic and medicinal chemistry. Our methods make possible, for the first time, the large-scale synthesis of enantioenriched diarylmethanols from aryl bromides. This method will be applied to the synthesis of enantiomerically enriched heterocycles bearing important pharmacophores, such as furans and pyridines. We have also developed several new routes to pyranones, furanosidic aldehydes, furans, and pyrroles. These medicinally important heterocycles can be prepared with high enantioselectivities using our methods. We have developed one-pot synthesis of a-hydroxy ketones, allylic alcohols, and substituted cyclopropanes from a versatile 1-alkenyl-1,1-bimetallic intermediate. These methods will be useful in complex molecule synthesis. The Specific Aims of this proposal are: I. Development of Direct Methods for Conversion of Aryl, Vinyl, and Alkyl Bromides to Enantioenriched Alcohols. II. Introduction of New Methods For Heterocycle Syntheses. III: Development of 1-Alkenyl-1,1-Bimetallic Reagents for Complex Molecule Synthesis. This project presents new methods to synthesize important chiral building blocks that were not easily accessible, but find utility in health-related applications, particularly in the synthesis of enantioenriched pharmaceutical agents.