Efficient Organocatalytic Hetero-Diels-Alder
Reactions of Activated Ketones under High Pressure for Direct Access
to δ-Lactones

Kaori Mori; Jacques Maddaluno; Keiji Nakano; Yoshiyasu Ichikawa; Hiyoshizo Kotsuki

doi:10.1055/s-0029-1217718

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Synlett 2009(14): 2346-2350
DOI: 10.1055/s-0029-1217718

LETTER

Efficient Organocatalytic Hetero-Diels-Alder Reactions of Activated Ketones under High Pressure for Direct Access to δ-Lactones [¹]

Kaori Mori^a, Jacques Maddaluno^b, Keiji Nakano^a, Yoshiyasu Ichikawa^a, Hiyoshizo Kotsuki*^a
^a Laboratory of Natural Product Chemistry, Faculty of Science, Kochi University, Akebono-cho, Kochi 780-8520, Japan
Fax: +81(888)448359; e-Mail: kotsuki@kochi-u.ac.jp;
^b IRCOF, CNRS UMR 6014 & FR 3038, Université de Rouen, 76821 Mont Saint-Aignan Cedex, France

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Publikationsverlauf

Received 20 May 2009
Publikationsdatum:
31. Juli 2009 (online)

Abstract
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Abstract

A general and efficient protocol for the high-pressure-promoted hetero-Diels-Alder reactions of activated ketones has been developed. The reactions are successfully achieved by thiourea-derived organocatalysts, and the desired adducts, convenient precursors of δ-lactones, are obtained in good to high yields.

Key words

Hetero-Diels-Alder reaction - activated ketones - δ-lactones - thiourea catalyst - high pressure

References and Notes

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15

General Procedure A mixture of diene (2, 1.0 mmol) and ketone (3, 0.25 mmol) in the presence of 1a (0.1 mmol) in toluene or CH₂Cl₂ (ca. 2.5 mL) was placed in a Teflon reaction vessel, and the mixture was allowed to react at 1.0 GPa and r.t. for 10 h. After the pressure was released, the mixture was concentrated and purified by silica gel column chromatog-raphy (elution with hexane-Et₂O) to afford the pure adduct 4.

18

Typically, treatment of 4a with excess Jones’ reagent in acetone (0 ˚C, 3 h) gave the corresponding dihydropyranone 5 in 60% yield: colorless needles (Scheme [²] ); mp 104-105 ˚C (hexane-CH₂Cl₂). FTIR (KBr): ν = 1745, 1718 cm^-¹. ^¹H NMR (400 MHz, CDCl₃): δ = 2.85 (1 H, dt, J = 18.2, 2.5 Hz), 3.49 (1 H, ddd, J = 18.2, 5.8, 1.0 Hz), 3.73 (3 H, s), 6.12 (1 H, ddd, J = 9.8, 2.5, 1.0 Hz), 6.91 (1 H, ddd, J = 9.8, 5.8, 2.5 Hz), 7.33-7.44 (3 H, m), 7.60-7.63 (2 H, m). ^¹³C NMR (100 MHz, CDCl₃): δ = 33.0, 53.4, 84.2, 121.8, 124.9 (2×), 128.7 (2×), 128.9, 137.1, 143.6, 162.2, 171.0. Anal. Calcd for C₁₃H₁₂O₄: C, 67.23; H, 5.21. Found: C, 67.13; H, 5.35.