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Synthesis 1990; 1990(4): 305-311
DOI: 10.1055/s-1990-26859
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Synthesis of 3-Alkoxyalkanoic Esters from Acetals. A Novel Application of Reformatsky Reagents in Asymmetric Synthesis

Tiziana Basile* , Emilio Tagliavini, Claudio Trombini, Achille Umani-Ronchi
  • *Dipartimento di Chimica "G. Ciamician", Università di Bologna, via Selmi, 2, I-40126 Bologna, Italy
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Publication Date:
17 September 2002 (online)

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3-Alkoxyalkanoic esters are directly obtained in high yield from the reaction of acetals with Reformatsky reagents in the presence of titanium(IV) chloride or diethyl ether-boron trifluoride complex in dichloromethane. The reaction of ethyl 4-bromo-2-butenoate is regioselective, affording the product formed by attack on the 4-position. With chiral acetals as substrates, up to 84% enantiomerically enriched 3-hydroxyalkanoic esters can be prepared.

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