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

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

Rights statement

• Permission granted by the author to include this thesis or dissertation in this repository. All rights reserved by the author. Please contact the author for information regarding the reproduction and use of this thesis or dissertation.

School	Emory College
Department	Chemistry
Degree	BS
Submission	Honors Thesis
Language	English
Research Field	Chemistry, Organic
Palavra-chave	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

Última modificação

Primary PDF

Thumbnail	Title	Date Uploaded	Actions
	Asymmetric Synthesis of 8-oxabicyclo[3.2.1]octane Derivatives Using a Chiral Dirhodium Catalyst ()	2018-08-28 15:12:34 -0400	Press to Select an action Download

Supplemental Files

Thumbnail	Title	Date Uploaded	Actions