Highly Enantioselective Reaction of α-Selenoorganolithium Compounds with Chiral Bis(oxazoline)s and Preparation of Enantioenriched Benzylidencyclohexanes
作者:Shuichi Nakamura、Takayuki Aoki、Takahiro Ogura、Libo Wang、Takeshi Toru
DOI:10.1021/jo048505l
日期:2004.12.1
The enantioselective reaction of α-seleno carbanions derived from bis(phenylseleno)acetal and bis(2-pyridylseleno)acetal in the presence of bis(oxazoline)s with various electrophiles gave products with high enantioselectivity. The enantioselective reaction of α-lithio benzyl 2-pyridyl selenide gave the products with stereochemistry reverse to that obtained in the reaction of α-lithio benzyl phenyl
在双(恶唑啉)存在下,由双(苯基硒基)缩醛和双(2-吡啶基硒基)缩醛衍生的α-硒基碳负离子与各种亲电试剂的对映选择性反应得到高对映选择性的产物。α-亚硫基苄基2-吡啶基硒化物的对映选择性反应产生的产物的立体化学与α-亚硫基苄基苯基硒化物的反应相反。机理研究表明,在-78°C下这些反应的对映体测定取决于动态热力学分辨率。将对映选择性反应用于制备富含对映体的烯烃和环氧化物。