4.4 Article

Electronic And Steric Effect Favored Selective Synthesis Of Asymmetric (-) N-Aryl Mandelamides

Journal

CHEMISTRYSELECT
Volume 4, Issue 48, Pages 14032-14035

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.201904614

Keywords

asymmetric transfer hydrogenation; alpha-hydroxyl amide; Ru-Teth-(TsDPEN) complex; steric and electronic effect; enantioselective reaction

Funding

  1. Department of Science and Technology (DST-INSPIRE), New Delhi, India

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This work reports selective synthesis of asymmetric (-) alpha-Hydroxyl Amides like N-aryl mandelamides via asymmetric transfer hydrogenation (ATH) of alpha-keto Amides like N-aryl benzoyl formamides using Ru-Tethered TsDPEN catalyst. The electronic and steric effect at ortho position leading to high enantioselectivity for ATH of carbonyl, sandwiched between two sp(2) carbon is studied. A wide range of mono and di ortho substituted alpha-hydroxyl amide is synthesized using this protocol with good enantioselectivity.

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