Knoevenagel Adducts as Trimethylenemethane Dipole Surrogates

Vertesaljai, Peter; Navaratne, Primali V.; Grenning, Alexander J.

doi:10.1002/ange.201508100

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Angewandte Chemie

2015

DOI: 10.1002/ange.201508100

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Knoevenagel Adducts as Trimethylenemethane Dipole Surrogates

Peter Vertesaljai

Primali V. Navaratne

Alexander J. Grenning

Abstract: Knoevenagel adducts derived from readily available acetoxyacetone and malonic acid derivatives served as trimethylenemethane surrogates for formal 1,3‐difunctionalization through a sequence of selective γ‐deprotonation/α‐alkylation and palladium(0)‐catalyzed allylic alkylation. Herein, we report the discovery and development of a three‐component 1,3‐difunctionalization of Knoevenagel adducts as well as a unique palladium(0)‐catalyzed branch‐selective allylic alkylation.

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Cited by 5 publications

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Oxygenated, polycyclic terpenoid natural products have important biological activities.Although total synthesis of such terpenes is widely studied, synthetic strategies that allow for controlled placement of oxygen atoms and other functionality remains achallenge.Herein, we present asimple,scalable, and tunable synthetic strategy to assemble terpenoid-like polycycloalkanes from cycloalkanones,m alononitrile,a nd allylic electrophiles,abundantly available reagent classes. Figure 1. Representativeoxygenatedt erpenoid natural products.

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Assembly of Terpenoid Cores by a Simple, Tunable Strategy

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An Enyne Cope Rearrangement Enables Polycycloalkane Synthesis from Readily Available Starting Materials

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Cyclohexanone‐derived Knoevenagel adducts (cyclohexylidenemalononitriles) and two different propargyl electrophiles serve as carbon sources for assembling diverse 6/7/5 tricycloalkanes, a common terpenoid framework. The sequence involves three unique reactions: 1) deconjugative propargylation, 2) one‐pot enyne Cope rearrangement/deconjugative propargylation, and 3) an allenic Pauson–Khand reaction.

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Assembly of Terpenoid Cores by a Simple, Tunable Strategy

et al. 2016

Self Cite

View full text Add to dashboard Cite

Oxygenated, polycyclic terpenoid natural products have important biological activities. Although total synthesis of such terpenes is widely studied, synthetic strategies that allow for controlled placement of oxygen atoms and other functionality remains a challenge. Herein, we present a simple, scalable, and tunable synthetic strategy to assemble terpenoid-like polycycloalkanes from cycloalkanones, malononitrile, and allylic electrophiles, abundantly available reagent classes.

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Knoevenagel Adducts as Trimethylenemethane Dipole Surrogates

Cited by 5 publications

References 43 publications

Assembly of Terpenoid Cores by a Simple, Tunable Strategy

Assembly of Terpenoid Cores by a Simple, Tunable Strategy

An Enyne Cope Rearrangement Enables Polycycloalkane Synthesis from Readily Available Starting Materials

Assembly of Terpenoid Cores by a Simple, Tunable Strategy

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