Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution.

Autor: Zatolochnaya OV; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com., Rodríguez S; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com., Zhang Y; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com., Lao KS; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com., Tcyrulnikov S; Department of Chemistry , University of Pennsylvania , Philadelphia , PA 19104 , USA . Email: marisa@sas.upenn.edu., Li G; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com., Wang XJ; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com., Qu B; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com., Biswas S; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com., Mangunuru HPR; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com., Rivalti D; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com., Sieber JD; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com., Desrosiers JN; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com., Leung JC; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com., Grinberg N; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com., Lee H; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com., Haddad N; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com., Yee NK; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com., Song JJ; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com., Kozlowski MC; Department of Chemistry , University of Pennsylvania , Philadelphia , PA 19104 , USA . Email: marisa@sas.upenn.edu., Senanayake CH; Chemical Development , Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Old Ridgebury Road , Ridgefield , CT 06877 , USA . Email: yongda.zhang@boehringer-ingelheim.com ; Email: sonrodrod@hotmail.com.
Jazyk: angličtina
Zdroj: Chemical science [Chem Sci] 2018 Apr 23; Vol. 9 (19), pp. 4505-4510. Date of Electronic Publication: 2018 Apr 23 (Print Publication: 2018).
DOI: 10.1039/c8sc00434j
Abstrakt: A new class of tunable heterophosphole dimeric ligands have been designed and synthesized. These ligands have enabled the first examples of Cu-catalyzed hydrogenation of 2-substituted-1-tetralones and related heteroaryl ketones via dynamic kinetic resolution, simultaneously creating two contiguous stereogenic centers with up to >99 : 1 dr and 98 : 2 er. The ligand-Cu complexes were isolated and characterized by single crystal X-ray, and DFT calculations revealed a novel heteroligated dimeric copper hydride transition state.
Databáze: MEDLINE
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