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- Title
Synthesis of Bridging Chiral p–tert‐Butylcalix[4]arenes with One and Two Carbamoyl Bridge‐Substituents through Anionic Ortho‐Fries Rearrangement
- Authors
Ma, Hao; Weng, Xiu‐Fang; Ren, Shan‐Shan; Tang, Zi‐Ying; Peng, Xin‐Bang; He, Yong; Zheng, Shuang; Wei‐LiDong; Li, Shao‐Yong
- Abstract
Bridging chiral p‐tert‐butylcalix[4]arenes (p‐t‐Bu‐BCC's) with different N‐substituted carbamoyl bridge‐substituents (N,N‐dimethylcarbamoyl, N,N‐diethylcarbamoyl and morpholinocarbonyl) were successfully prepared through anionic ortho‐Fries rearrangement from mono‐O‐carbamates of 1,3‐dipropyl‐p‐tert‐butylcalix[4]arene in 65–75% yield. In addition, p‐t‐Bu‐BCC with two N,N‐dimethylcarbamoyl bridge‐substituents was produced by this method from mono‐O‐carbamate of p‐t‐Bu‐BCC with one N,N‐dimethylcarbamoyl bridge‐substituent in 71% yield. However, the synthesis of p‐t‐Bu‐BCC with additional carbamoyl bridge‐substituents using this method could not be attempted, as the required rearrangement precursor failed to be synthesized. Finally, the racemic p‐t‐Bu‐BCC with morpholinocarbonyl bridge‐substituent was optically resolved into a pair of enantiomers, whose absolute configurations were determined through ROESY analysis and ECD comparison.
- Publication
ChemistrySelect, 2020, Vol 5, Issue 21, p6274
- ISSN
2365-6549
- DOI
10.1002/slct.202000891