化学
对映选择合成
弗里德尔-克拉夫茨反应
催化作用
磷酸
芳基
有机化学
药物化学
立体化学
烷基
作者
Masahiro Terada,Shun Yokoyama,Keiichi Sorimachi,Daisuke Uraguchi
标识
DOI:10.1002/adsc.200700151
摘要
Abstract A highly enantioselective 1,2‐aza‐Friedel–Crafts reaction of N ‐ tert ‐butyldimethylsilylindole with N ‐ tert ‐butoxycarbonyl aromatic imines is demonstrated using a BINOL‐derived monophosphoric acid catalyst. The present approach provides efficient access to 3‐indolylmethaneamines with aryl substituents in excellent enantioselectivities (up to 98 % ee ). An inversion in the sense of enantioselection was found between monophosphoric acid catalysts bearing different substituents introduced at the 3,3′‐position of binaphthyl backbone. We also calculated the three‐dimensional structure of the monophosphoric acid catalysts to speculate on the inversion of the stereochemical outcome.
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