Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC, 27599-3290, USA.
Angew Chem Int Ed Engl. 2017 Jul 17;56(30):8805-8808. doi: 10.1002/anie.201704226. Epub 2017 Jun 20.
The addition of terminal alkynes to racemic β-stereogenic α-keto esters was achieved in high levels of stereoselectivity, affording versatile tertiary propargylic alcohols containing two stereocenters. This environmentally benign enantioconvergent reaction proceeds with perfect atom economy, requires no solvent, and is catalyzed by a non-toxic zinc salt. The alkyne moiety can be leveraged in downstream transformations including hydrogenation to the corresponding saturated tertiary alcohol, which represents the product of a formal enantioconvergent aliphatic nucleophile addition.
手性β-立体选择性α-酮酯与末端炔烃的加成反应以高立体选择性实现，得到了含有两个手性中心的多功能仲丙炔醇。这种环境友好的对映体转化反应具有完美的原子经济性，无需溶剂，且由无毒的锌盐催化。炔基部分可用于下游转化，包括加氢得到相应的饱和仲醇，这代表了一种形式上的对映体转化的脂肪族亲核加成产物。
