Nonnatural Amino Acid Synthesis by Using Carbon–Hydrogen Bond Functionalization Methodology


  • We thank the Welch Foundation (Grant No. E-1571), NIGMS (Grant No. R01GM077635), and Camille and Henry Dreyfus Foundation for supporting this research. We also thank Dr. James Korp for collecting and solving the X-ray structure of 21.


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Taking direction well: Substituted phenylalanine derivatives were prepared by C[BOND]H bond functionalization (see scheme). The syntheses are highly convergent and employ an N-phthaloylalanine with a 2-thiomethylaniline directing group. The use of an 8-aminoquinoline directing group allows for the diarylation of methyl and the diastereoselective arylation of methylene groups.