Abstract
We report a highly efficient and practical protocol for palladium-catalyzed N-quinolylcarboxamide (AQ)-directed arylation of the unactivated β-C(sp3)-H bonds of alanine with aryl iodides at room temperature. For the first time, a broad range of easily accessible aryl iodides can be installed onto the β-methyl group of AQ-coupled phthaloyl alanine mono-selectively, providing both natural and unnatural aromatic α-amino acids. Access to these mono-arylated compounds enables subsequent AQ-directed diastereoselective C-H functionalization, allowing the preparation of various β-disubstituted aromatic α-amino acids in a programmable manner.
Original language | English (US) |
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Pages (from-to) | 3952-3957 |
Number of pages | 6 |
Journal | Chemical Science |
Volume | 5 |
Issue number | 10 |
DOIs | |
State | Published - Oct 2014 |
All Science Journal Classification (ASJC) codes
- General Chemistry