Diastereoselective addition of organozinc and organomagnesium reagents to 2-(2 '-pyrimidyl)ferrocenecarbaldehyde

作者：Omedes Marta; Gomez Sal Pilar; Andries Julien; Moyano Albert^*

来源：Tetrahedron, 2008, 64(18): 3953-3959.

DOI：10.1016/j.tet.2008.02.056

• addition reactions
• asymmetric synthesis
• metallocenes
• organometallic reagents
• stereoselectivity

Addition of diisopropylzinc, diethylzinc, and isopropylmagnesium chloride to readily available 2-(2'-pyrimidyl)ferrocenecarbaldehyde takes place with high diastereoselectivity to afford exclusively the alpha-ferrocenyl alcohol of (R*,pR*) configuration. On the other hand, the addition of ethyl- and methylmagnesium bromide leads to diastereomeric mixtures in which the major isomer has the (S*,pR*) configuration. A unified mechanistic model accounting for this stereochemical outcome is proposed.

• 出版日期2008-4-28