Synthesis of highly functionalized pyrrolidines via a selective iodide-mediated ring expansion of methylenecyclopropyl amides.

doi:10.1021/jo802049u

Paper

Synthesis of highly functionalized pyrrolidines via a selective iodide-mediated ring expansion of methylenecyclopropyl amides.

Published Oct 8, 2008 · Mark E. Scott, M. Lautens

The Journal of organic chemistry

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30

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Abstract

This manuscript describes a highly selective iodide-mediated, tandem Mannich/cyclization to afford trans-2,3-disubstituted pyrrolidines from methylenecyclopropyl amides in good to excellent yields and selectivities. The reaction scope has been drastically expanded to include a wide array of aromatic, heteroaromatic and alpha,beta-unsaturated imines, as well as a variety of methylenecyclopropyl amides. Additionally, mechanistic studies were carried out to ascertain the nature of the ring-opening/ring-closing mechanism using deuterated substrates. Results from these studies indicate that the primary mechanism is an S(N)2/S(N)2 ring opening/ring closing and that iodine- or iodide-mediated isomerization of the iodo enolate is likely occurring.

Study Snapshot

Selective iodide-mediated ring expansion of methylenecyclopropyl amides allows for the efficient synthesis of trans-2,3-disubstituted pyrrolidines with good to excellent yields and selectivities.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis of highly functionalized pyrrolidines via a selective iodide-mediated ring expansion of methylenecyclopropyl amides.

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References

Citations

Applications of aryl-sulfinamides in the synthesis of N-heterocycles

Aryl-sulfinamides provide a versatile method for synthesising diverse N-heterocycles, offering access to natural products and therapeutically important compounds.

Magnesium Halide‐Catalyzed Synthesis of Oxaspiro[2.5]octenes from a Methylenecyclopropane and Acyl Cyanoalkenes

Magnesium halide-catalyzed annulation of methylenecyclopropanes with acyl cyanoalkenes yields excellent yields of oxaspiro[2.5]octenes, which can be transformed into 4H-pyran at higher temperatures

1,8-Diazabicyclo[5.4.0]undec-7-ene-mediated formation of N-sulfinyl imines

This study developed a facile method for preparing various N-sulfinyl imines using 1,8-diazabicyclo[5.4.0]undec-7-ene and tert-butanesulfinamide at room temperature, resulting in excellent yields without acids, metals,

Thermally-induced intramolecular [2 + 2] cycloaddition of acrylamide-tethered alkylidenecyclopropanes.

This study demonstrates a highly regio- and diastereoselective synthetic method for cyclobutane-containing spiro[2.3]hexane fused with six-membered hetero-cycles using thermally-induced intramolecular cycloaddition of

Catalytic Annulation of Diethyl Methylenecyclopropane-1,1-dicarboxylate with 1,1-Dicyanoalkenes.

The Mg-Sn catalytic system effectively catalyzes the selective formation of cyclopentylidenemalonates and spiro[2,3]hexane-1,1-dicarboxylates from diethyl methylenecyclopropane-1,1