Event Title

Iodine Mediated Rearrangement of Diphenyldiallyl Silane

Research Mentor(s)

Gregory O'Neil

Description

The iodine-mediated rearrangement of diallyldiphenyl silane yielded a stereocenter at the site of a new carbon-carbon bond. In an attempt to isolate the enantiomers, the racemic mixture underwent a Sharpless Asymmetric Dihydoxilation and intramolecular ring closure to create two distinct diastereomers. Separation of the diastereomers was achieved using column chromatography on silica. The stereochemistry of the two compounds was identified by using COSy and NOESy techniques. This structure is a versatile precursor for the synthesis of various natural products.

Document Type

Event

Start Date

May 2018

End Date

May 2018

Location

Chemistry

Rights

Copying of this document in whole or in part is allowable only for scholarly purposes. It is understood, however, that any copying or publication of this document for commercial purposes, or for financial gain, shall not be allowed without the author’s written permission.

Language

English

Format

application/pdf

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Iodine Mediated Rearrangement of Diphenyldiallyl Silane

Chemistry

The iodine-mediated rearrangement of diallyldiphenyl silane yielded a stereocenter at the site of a new carbon-carbon bond. In an attempt to isolate the enantiomers, the racemic mixture underwent a Sharpless Asymmetric Dihydoxilation and intramolecular ring closure to create two distinct diastereomers. Separation of the diastereomers was achieved using column chromatography on silica. The stereochemistry of the two compounds was identified by using COSy and NOESy techniques. This structure is a versatile precursor for the synthesis of various natural products.