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Azobenzene-based unnatural amino acid motifs were synthesized via Pd(II)-catalyzed diastereoselective C(sp3)–H arylation of amino acid carboxamides with iodoacetanilides and Mills azo coupling. [ABSTRACT FROM AUTHOR]

We highlight the reported developments of the palladium-catalyzed C–H activation and functionalization of the inactive/unreactive prochiral C(sp3)–H bonds of aliphatic and alicyclic compounds. There exist numerous classical methods for generating contiguous stereogenic centers in a compound with a high degree of stereocontrol. Along similar lines, the Pd(II)-catalyzed, directing group-aided functionalization of inactive prochiral/diastereotopic C(sp3)–H bonds have been exploited to accomplish the stereoselective construction of stereo-arrays in organic compounds. We present a concise discussion on how specific strategies consisting of Pd(II)-catalyzed, directing group-aided C(sp3)–H functionalization have been utilized to generate two or more stereogenic centers in aliphatic and alicyclic compounds. [ABSTRACT FROM AUTHOR]