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Start Over Author "Xun Wei" Journal tetrahedron: asymmetry
6 results on '"Xun Wei"'

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

Author

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

Subjects
Chiral auxiliary, Chemistry, Silica gel, Component (thermodynamics), Organic Chemistry, Enantioselective synthesis, Diastereomer, General Medicine, Catalysis, Inorganic Chemistry, chemistry.chemical_compound, Product (mathematics), Organic chemistry, Physical and Theoretical Chemistry, Conjugate
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.

Published
2003
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