Highly Diastereoselective Iron-Mediated C(sp2)C(sp3) Cross-Coupling Reactions between Aryl Grignard Reagents and Cyclic Iodohydrine Derivatives
作者:Andreas K. Steib、Tobias Thaler、Kimihiro Komeyama、Peter Mayer、Paul Knochel
DOI:10.1002/anie.201007187
日期:2011.3.28
trans‐2‐Arylcycloalcohol derivatives are obtained in high diastereoselectivity by the iron‐mediated cross‐coupling of cyclic TBS‐protected iodohydrines with aryl Grignard reagents (see scheme; TBS=tert‐butyldimethylsilyl). The stereoconvergent cross‐coupling of a chiral TBS‐protected 2‐iodocyclohexanol provides the 2‐arylcyclohexanols with no loss of stereochemical purity, and is a valuable alternative
反式-2-芳基环醇衍生物是通过铁介导的环状TBS保护的碘代醇与芳基格利雅试剂的高非对映选择性而获得的(参见方案; TBS =叔丁基二甲基甲硅烷基)。手性TBS保护的2-碘代环己醇的立体收敛交叉偶联提供了2-芳基环己醇,而又不损失立体化学纯度,并且是对称环氧化物的对映选择性开环的有价值的替代方法。