Solid phase synthesis of allylic alcohols via the Baylis-Hillman reaction.
An efficient method for the solid phase synthesis of allylic alcohols via the Baylis-Hillman reaction has been developed. In the presence of DABCO or 3-quinuclidinol the coupling of resin bound acrylic acid with different aldehydes yields allylic alcohols. Aldehydes with different reactivity were used and gave modest to excellent yields upon simply varying the base or the reaction time. The allylic alcohols were reacted with primary amines to form 1,3-aminoalcohols.
Institut für Organische Chemie, Eberhard-Karls-Universität Tübingen, Germany.
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Richter
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Jung
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D002851:Chromatography, High Pressure Liquid; D015195:Drug Design; D007202:Indicators and Reagents; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D020005:Propanols / Q000138:chemical synthesis* / Q000737:chemistry; D018629:Spectrometry, Mass, Secondary Ion; D013329:Structure-Activity Relationship
D000447:Aldehydes; D007202:Indicators and Reagents; D020005:Propanols; C006463:allyl alcohol