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Synlett 2017; 28(06): 633-639
DOI: 10.1055/s-0036-1589954
DOI: 10.1055/s-0036-1589954
synpacts
Simplifying Complex Scaffold Synthesis: Knoevenagel Adduct Allyl Anions as Easily Generated Multifunctional Reagents
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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For recent examples of alkylidnemalonate conjugate addition, see:
For recent examples of alkylidenemalonate cycloaddition, see:
Seminal reports of γ-alkylation of Knoevenagel adducts:
Additional examples of γ-alkylation of Knoevenagel adducts:
Examples of γ-alkylation/deconjugative α-alkylation:
For examples of related [3,3] Cope rearrangements, see: