1. Ir/Cu Dual Catalysis: Enantio- and Diastereodivergent Access to α,α-Disubstituted α-Amino Acids Bearing Vicinal Stereocenters
- Author
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Rui He, Jingke Fu, Wanbin Zhang, Xiaohong Huo, and Jiacheng Zhang
- Subjects
Allylic rearrangement ,Stereochemistry ,Bioactive molecules ,Imine ,Iridium ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Catalysis ,Stereocenter ,chemistry.chemical_compound ,Colloid and Surface Chemistry ,Reactivity (chemistry) ,Amino Acids ,chemistry.chemical_classification ,010405 organic chemistry ,Esters ,Stereoisomerism ,Dipeptides ,General Chemistry ,0104 chemical sciences ,Amino acid ,Allyl Compounds ,chemistry ,Imines ,Copper ,Vicinal - Abstract
We describe a fully stereodivergent synthesis of a range of α,α-disubstituted α-amino acids via an Ir/Cu-catalyzed α-allylation of readily available imine esters. The introduction of a Cu-Phox complex-activated imine ester into the chiral iridium-catalyzed allylic allylation process is crucial for its high reactivity and excellent enantio- and diastereoselectivity (up to >99% ee and >20:1 dr). Importantly, the two chiral catalysts allow for full control over the configuration of the stereocenters, affording all stereoisomers of the desired products. The utility of this methodology was demonstrated by synthesizing dipeptides and analogues of bioactive molecules in a stereodivergent manner.
- Published
- 2018
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