Concellón José M, Huerta Mónica
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, C. Julián Clavería 8, 33071 Oviedo, Spain.
J Org Chem. 2005 Jun 10;70(12):4714-9. doi: 10.1021/jo0504969.
A samarium diiodide promoted addition of aromatic or aliphatic beta-substituted-alpha-halo-alpha,beta-unsaturated esters 1 or 3 to both ketones (in THF) and aldehydes (in acetonitrile) led to (Z)-2-(1-hydroxyalkyl)-2,3-alkenoates 2 and 4 in good yields and very high stereoselectivity. This method constitutes an efficient and valuable alternative to the synthesis of Baylis-Hillman adducts. A mechanism is proposed to explain this transformation.
二碘化钐促进的芳族或脂肪族β-取代的α-卤代-α,β-不饱和酯1或3与酮（在四氢呋喃中）和醛（在乙腈中）的加成反应，以良好的产率和非常高的立体选择性生成(Z)-2-(1-羟烷基)-2,3-链烯酸酯2和4。该方法构成了合成贝利斯-希尔曼加合物的一种有效且有价值的替代方法。提出了一种机理解释这种转化。
