化学
立体中心
手性(物理)
芳基
维蒂希反应
酒
试剂
催化作用
立体化学
对映选择合成
醛
组合化学
药物化学
有机化学
烷基
手征对称破缺
量子力学
物理
Nambu–Jona Lasinio模型
夸克
作者
Long‐Sheng Zheng,Kezhi Jiang,Yuan Deng,Xing‐Feng Bai,Guang Gao,Feng‐Lei Gu,Li‐Wen Xu
标识
DOI:10.1002/ejoc.201201301
摘要
Abstract We have demonstrated a highly diastereoselective synthesis of optically pure Ar‐BINMOL‐derived diols and their analogues. The present study demonstrates a unique cascade chirality transfer in a [1,2]‐Wittig rearrangement that leads to chiral diols with three stereogenic centers, which include a chiral sp 3 center at the alcohol and C 2 ‐axial chirality. Screening these ligands in the arylation of aromatic aldehydes with Grignard reagents shows that the naphthyl‐substituted BINMOL promotes the aryl transfer reaction in good yields (70–92 %) and moderate‐to‐good enantioselectivities (up to 72 % ee ), and a series of control experiments substantiates that the axial chirality and the chiral sp 3 center at the alcohol of the Ar‐BINMOLs are the pivotal enantioselectivity‐controlling structure elements. In addition, this study demonstrated the importance of the chiral sp 3 center at the alcohol on Ar‐BINMOL for the aryl transfer reaction. Finally, we found that the chiral Ar‐BINMOL ligand 2h mediated the titanium‐promoted 1,2‐addition of MeMgBr to aldehydes to give the desired products in good yields with excellent enantioselectivities (up to 92 % ee ).
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