Asymmetric synthesis of chiral β-iodo Baylis-Hillman esters using MgI2 as promoter via a one-pot three-component reaction

Han Xun Wei, Dianjun Chen, Xin Xu, Guigen Li, Paul W. Paré

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Abstract

An asymmetric synthesis of β-iodo-α-(hydroxyalkyl)acrylates has been developed involving conjugate addition of I- to menthyl propiolates to give β-iodo allenolate intermediates which undergo 1,2-addition to form β-iodo Baylis-Hillman products. Modest diastereoselectivities (37-58% de) and excellent yields (80-87%) were obtained when (1R,2S,5R)-(-)-menthol was used as a chiral auxiliary. The two diastereoisomers of the product were separated by silica gel chromatography to give diastereomerically pure products.

Original languageEnglish
Pages (from-to)971-974
Number of pages4
JournalTetrahedron Asymmetry
Volume14
Issue number8
DOIs
StatePublished - Apr 18 2003

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