Extremely Active Organocatalysts Enable a Highly Enantioselective Addition of Allyltrimethylsilane to Aldehydes
作者:Philip S. J. Kaib、Lucas Schreyer、Sunggi Lee、Roberta Properzi、Benjamin List
DOI:10.1002/anie.201607828
日期:2016.10.10
The enantioselective allylation of aldehydes to form homoallylic alcohols is one of the most frequently used carbon–carbon bond‐forming reaction in chemical synthesis and, for several decades, has been a testing ground for new asymmetric methodology. However, a general and highly enantioselective catalytic addition of the inexpensive, nontoxic, air‐ and moisture‐stable allyltrimethylsilane to aldehydes
醛的对映选择性烯丙基化形成均烯丙基醇是化学合成中最常用的碳-碳键形成反应之一,并且几十年来,它一直是新的不对称方法的试验场。但是,Hosomi-Sakurai 1反应是将廉价,无毒,对空气和湿气稳定的烯丙基三甲基硅烷进行通用且高度对映选择性的催化反应(Hosomi-Sakurai 1反应)仍然难以实现。2 3本文报道了高酸性的亚氨基二磷酸亚氨酸酯基序(IDPi)的设计和合成,其能够进行这种转化,从而以0.05至2.0mol%的催化剂负载量转化具有芳族和脂族基团的各种醛,具有优异的对映选择性。我们合理构造的催化剂具有高度可调的活性位点,可以选择性地处理小底物,因此有望在各种其他具有挑战性的化学反应中使用。