Asymmetric Synthesis of 8-oxabicyclo[3.2.1]octane Derivatives Using a Chiral Dirhodium Catalyst Public

Abstract

Asymmetric Synthesis of 8-oxabicyclo[3.2.1]octane Derivatives Using a Chiral Dirhodium
Catalyst
By Adam Levinson

The 8-oxabicyclo[3.2.1]octane molecular structure is a very synthetically useful motif for the
construction of several complex natural products. Although it has previously been demonstrated
that this structure can be synthesized asymmetrically in high yields using the Rh(II)-catalyzed
tandem cyclopropanation/Cope-rearrangement with the aid of a chiral auxiliary, this reaction has
not demonstrated high enantioselectivity with the use of a chiral dirhodium catalyst. This study
has focused primarily on trying to achieve a highly enantioselective synthesis of 8-
oxabicyclo[3.2.1] derivatives using the chiral Rh2(S-PTAD)4 catalyst. Furthermore, this study
gives insight into the discrepancies between the stereochemical outcome for the tandem
cyclopropanation/Cope-rearrangement of furan substrates catalyzed by Rh2(S-DOSP)4 versus
Rh2(S-PTAD)4.

Table of Contents

Table of Contents
Introduction………………………………………………………………………………………1
Synthesis of Diazo Compounds…………………………………………………………………12
Optimization Process……….…………………………………………………………………...14
Synthesis of Furan Substrates………………………………………………………………..….17
Synthesis of 8-oxabicyclo[3.2.1]octane Derivatives……………………………………………19
Discussion/Conclusions…………………………………………………………………………24
Experimental Data…………………………………………………….....……………………...28

About this Honors Thesis

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School	Emory College
Department	Chemistry
Degree	BS
Submission	Honors Thesis
Language	English
Research Field	Chemistry, Organic
Mot-clé	Organic Chemistry Asymmetric Catalysis Rhodium Catalysis
Committee Chair / Thesis Advisor	Davies, Huw, Emory University
Committee Members	McDonald, Frank, Emory University Stokes, Darrell R, Emory University

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