Catalytic Asymmetric Synthesis of Hydroxy Enol Ethers: Approach to a Two-Carbon Homologation of Aldehydes
作者:Sang-Jin Jeon、Young K. Chen、Patrick J. Walsh
DOI:10.1021/ol050255n
日期:2005.4.1
[reaction: see text] Hydroboration of ethoxy acetylene, transmetalation to zinc, and addition to aldehydes in the presence of a chiral amino alcohol ligand (MIB) affords hydroxy enol ethers with high ee. The resultant enantiomerically enriched hydroxy enol ethers were converted to protected hydroxy aldehydes, a useful synthetic building block for the construction of a variety of polyoxygenated natural
[反应:见正文]在手性氨基醇配体(MIB)的存在下,乙氧基乙炔的氢硼化,重金属化成锌,以及在醛中的加成,提供了具有高ee值的羟基烯醇醚。将所得对映异构体富集的羟基烯醇醚转化为受保护的羟基醛,这是用于构建各种多加氧天然产物的有用的合成构件。另外,研究了对-和反-1,3-二醇的非对映选择性形成。