Asymmetric, Organocatalytic Bromolactonization of Allenoic Acids

Michael Wilking; Constantin G. Daniliuc; Ulrich Hennecke

doi:10.1055/s-0034-1378278

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(12): 1701-1704
DOI: 10.1055/s-0034-1378278

letter

Asymmetric, Organocatalytic Bromolactonization of Allenoic Acids

Michael Wilking

Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstr. 40, 48149 Münster, Germany Fax: +49(251)8336523 eMail: ulrich.hennecke@uni-muenster.de

,

Constantin G. Daniliuc

Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstr. 40, 48149 Münster, Germany Fax: +49(251)8336523 eMail: ulrich.hennecke@uni-muenster.de

,

Ulrich Hennecke*

Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstr. 40, 48149 Münster, Germany Fax: +49(251)8336523 eMail: ulrich.hennecke@uni-muenster.de

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Abstract

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Abstract

Asymmetric, reagent-controlled bromolactonizations of allenoic acids have been achieved by using (DHQD)₂PHAL as catalyst. A range of substrates can be cyclized in good yields and moderate to good enantioselectivities under operationally simple conditions.

Key words

allenes - asymmetric synthesis - cyclization - electrophilic addition - halogenation

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Referenzen

References and Notes

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13 CCDC-992322 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
14 A more extensive table of reaction conditions can be found in the Supporting Information.
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16 Enantioselective Halolactonization using 1,3-Dibromo-5,5-dimethylhydantoin (DBDMH); General Procedure (Conditions A): In a flame-dried Schlenk tube, the corresponding carboxylic acid (0.300 mmol, 1.0 equiv), benzoic acid (36.6 mg, 0.300 mmol, 1.0 equiv) and (DHQD)₂PHAL (23.4 mg. 30.0 μmol, 10 mol%) were dissolved in anhydrous CHCl₃/n-hexane (1:1, 6 mL), cooled to –30 °C and stirred for 15 min. DBDMH (103 mg, 0.360 mmol, 1.2 equiv) was added and stirring was continued at that temperature for 15 h. Sat. aq Na₂S₂O₃ (6 mL) was added to the reaction mixture and the aqueous layer was extracted with CH₂Cl₂ (3 × 10 mL). The combined organic layers were dried over Na₂SO₄, filtered, and the solvents were removed in vacuo. Purification by flash chromatography afforded the desired cyclization product.
17 The isolated yield of 5b was surprisingly low because full conversion of the starting material was observed and no detectable side products were formed (6-endo cyclization product was not formed). The reason for the low mass balance is unclear. Similar observations were made for 5d and 5e.
18 Enantioselective Halolactonization using N-Bromosuccinimide (NBS; General Procedure (Conditions B): In a flame-dried Schlenk tube, the corresponding carboxylic acid (0.300 mmol, 1.0 equiv) and (DHQD)₂PHAL (23.4 mg. 30.0 μmol, 10 mol%) were dissolved in anhydrous CHCl₃/n hexane (1:1, 6 mL), cooled to –30 °C and stirred for 15 min. NBS (64.1 mg, 0.360 mmol, 1.2 equiv) was added and stirring was continued at that temperature for 15 h. Sat. aq Na₂S₂O₃ (6 mL) was added to the reaction mixture and the aqueous layer was extracted with CH₂Cl₂ (3 × 10 mL). The combined organic layers were dried over Na₂SO₄, filtered, and the solvents were removed in vacuo. Purification by flash chromatography afforded the desired cyclization product.

Zusatzmaterial

Supporting Information