Title of article
Expedient synthesis of β,β-disubstituted α-methylenepropionates
Author/Authors
Kallolmay Biswas، نويسنده , , Christoph B?rner، نويسنده , , Josepe Gimeno، نويسنده , , Paul J. Goldsmith، نويسنده , , Daniella Ramazzotti، نويسنده , , Angela L.K. So، نويسنده , , Simon Woodward، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2005
Pages
10
From page
1433
To page
1442
Abstract
Baylis–Hillman alcohols are excellent sources of the allylic halides ArCHdouble bond; length as m-dashCH(CH2X)(CO2R) (X=Br, Cl; R1=Me, Et, But). The Z double bond isomers are attained in high isomeric purity (>14:1, Z/E). The halides are chemo- and regiospecifically transformed into the acrylates (ArCHR2)C(double bond; length as m-dashCH2)(CO2R1) on treatment with Zn(R2)2 (R2=Me, Et, CH2TMS, CH2SiMe2OMe) or PrZnBr in the presence of catalytic amounts of copper(I) salts (0.5–20 mol%) in high yield.
Keywords
Baylis–Hillman , copper , SN2? , Organozinc , Allylic substitution
Journal title
Tetrahedron
Serial Year
2005
Journal title
Tetrahedron
Record number
1088367
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