relation: http://d-scholarship-dev.library.pitt.edu/16662/
title: Catalytic Asymmetric Claisen Rearrangements. The Development of Ru(II)-Catalyzed Formal [3,3] Sigmatropic Rearrangements and Related Enolate Allylation Reactions
creator: Geherty, Maryll / E.
description: The Claisen rearrangement, a [3,3] sigmatropic rearrangement, remains an important method for the construction of C-C bonds nearly a century after its discovery.  However, methods to affect a catalytic and asymmetric variant of this reaction are rare.   A transition metal/Lewis acid co-catalyst system (Ru(II)-B(III)) has been successfully employed to affect an enantioselective, and diastereoselective Claisen rearrangement of simple, achiral, allyl vinyl ethers without the need for auxiliary functionality to assist in substrate-catalyst association. In addition, we have developed a complementary ruthenium catalyzed enolate allylic alkylation reaction that forms Claisen-like products, without the need to synthesize allyl vinyl ethers. 
date: 2013-01-25
type: University of Pittsburgh ETD
type: PeerReviewed
format: application/pdf
language: en
identifier: http://d-scholarship-dev.library.pitt.edu/16662/1/Maryll_Geherty_ETD_Thesis_4.pdf
identifier:   Geherty, Maryll / E.  (2013) Catalytic Asymmetric Claisen Rearrangements. The Development of Ru(II)-Catalyzed Formal [3,3] Sigmatropic Rearrangements and Related Enolate Allylation Reactions.  Doctoral Dissertation, University of Pittsburgh.    (Unpublished)