Synlett 2017; 28(06): 633-639
DOI: 10.1055/s-0036-1589954
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© Georg Thieme Verlag Stuttgart · New York

Simplifying Complex Scaffold Synthesis: Knoevenagel Adduct Allyl Anions as Easily Generated Multifunctional Reagents

Alexander J. Grenning*
Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL 32611-7200, USA   Email: grenning@ufl.edu
› Author Affiliations
Further Information

Publication History

Received: 08 December 2016

Accepted after revision: 04 January 2017

Publication Date:
30 January 2017 (online)

Abstract

Knoevenagel adduct allyl anions are easily generated and can serve as platforms for formal 1,3-difunctionalization. Summarized herein are a variety of reaction pathways that can be harnessed for multistep synthesis with emphasis on carbocycle synthesis.

1 Introduction

2 Formal 1,3-Difunctionalization Reactivity Modes: An Overview

3 γ-Alkylation/Deconjugative α-Alkylation

4 Deconjugative α-Alkylation/Pairing Sequences

5 Deconjugative α-Alkylation/Allylic Substitution

6 Deconjugative α-Alkylation/Allylic Transposition/Deconjugative α-Alkylation

7 Future Directions

8 Conclusions

 
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