Title

Studies Directed Toward the Synthesis of Enantioenriched Unsaturated Cyanohydrins and their Application in an Imidate [3,3] Sigmatropic Shift.

Authors

Summer Collier

Document Type

Article

Publication Date

2000

Abstract

The overarching goal of this research is the development of synthetic methodologies that permit facile, enantiocontrolled access to molecules of biological importance. A one step reaction forms imidate (3) from its corresponding aldehyde (1) using HCN dissolved in ether, trichloroacetonitrile and DBU as a catalyst. This racemic reaction has allowed for the mass production of (3) to work out the conditions of the palladium reaction. (3) can also be derived from enantiomerically pure unsaturated cyanohydrins (2) upon treatment with trichloroacetonitrile and DBU. Upon exposure to a palladium(II) catalyst, 3 undergoes a stereospecific [3,3] rearrangement to form the related acetamide (4). To date, this reaction has been shown to form only trans double-bond products. These highly functionalized products offer great versatility as chiral building blocks for the preparation of enantioenriched pharmaceutical compounds.

Advisor

Donald Deardorff

Department

chem

Support

American Chemical Society-Petroleum Research Fund

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