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

Alexander J. Grenning

doi:10.1055/s-0036-1589954

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

Alexander J. Grenning

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

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.

Original language	English (US)
Article number	st-2016-p0830-sp
Pages (from-to)	633-639
Number of pages	7
Journal	Synlett
Volume	28
Issue number	6
DOIs	https://doi.org/10.1055/s-0036-1589954
State	Published - Apr 1 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
© Georg Thieme VerlagStuttgart · New York.

Keywords

1,3-difunctionalization
Knoevenagel adducts
allyl anions
conjunctive reagents
deconjugative α-alkylation

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10.1055/s-0036-1589954

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title = "Simplifying Complex Scaffold Synthesis: Knoevenagel Adduct Allyl Anions as Easily Generated Multifunctional Reagents",

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.",

keywords = "1,3-difunctionalization, Knoevenagel adducts, allyl anions, conjunctive reagents, deconjugative α-alkylation",

author = "Grenning, {Alexander J.}",

note = "Publisher Copyright: {\textcopyright} Georg Thieme VerlagStuttgart · New York.",

year = "2017",

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doi = "10.1055/s-0036-1589954",

language = "English (US)",

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TY - JOUR

T1 - Simplifying Complex Scaffold Synthesis

T2 - Knoevenagel Adduct Allyl Anions as Easily Generated Multifunctional Reagents

AU - Grenning, Alexander J.

N1 - Publisher Copyright: © Georg Thieme VerlagStuttgart · New York.

PY - 2017/4/1

Y1 - 2017/4/1

N2 - 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.

AB - 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.

KW - 1,3-difunctionalization

KW - Knoevenagel adducts

KW - allyl anions

KW - conjunctive reagents

KW - deconjugative α-alkylation

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ER -

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

Abstract

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Keywords

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