立体中心
亲核细胞
化学
吡啶
催化作用
产量(工程)
有机化学
对映选择合成
组合化学
材料科学
冶金
作者
Ming‐Sheng Xie,Ye‐Fei Zhang,Shuxian Meng,Xin Wu,Gui‐Rong Qu,Hai‐Ming Guo
标识
DOI:10.1002/anie.201812864
摘要
Abstract A DMAP‐ N ‐oxide, featuring an α‐amino acid as the chiral source, was developed, synthesized and applied in asymmetric Steglich rearrangement. A series of O‐acylated azlactones afforded C‐acylated azlactones possessing a quaternary stereocenter in high yields (up to 97 % yield) and excellent enantioselectivities (up to 97 % ee ). Compared to the widespread use of pyridine nitrogen, which serves as the nucleophilic site in the asymmetric acyl transfer reaction, we discovered that chiral DMAP‐ N ‐oxides, in which the oxygen now acts as the nucleophilic site, are efficient acyl transfer catalysts. Our finding might open a new door for the development of chiral DMAP‐ N ‐oxides for asymmetric acyl transfer reactions.
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