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A New, Efficient and Stereocontrolled Synthesis of Trisubstituted Alkenes via Functionalized Acrylic Esters

✍ Scribed by Dr. Jürgen Rabe; Prof. H. M. R. Hoffmann

Publisher
John Wiley and Sons
Year
1983
Tongue
English
Weight
231 KB
Volume
22
Category
Article
ISSN
0044-8249

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✦ Synopsis

Typical example: (3-Formylpropyl)benzoate 2c (19.2 g, 0.1 mol) was mixed with methyl acrylate 3 (13 g; 14 mL; 0.15 mol). After addition of DABCO (1.6 g, 0.015 mol) the resulting homogeneous mixture was allowed to stand at room temperature until 2c was no longer detectable (cu. 7 days). The remaining methyl acrylate was removed on a rotary evaporator, the residue taken up in ether (100 mL) and washed with 10% aqueous hydrochloric acid (SO mL), and the ether phase washed with water and dried over MgSO.,. After removal of the solvent spectroscopically pure product 4c (26.4 g, 95%) rernained.-90 MHz 'H-NMR (CDClp, TMS):

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