Asymmetric Ruthenium‐Catalyzed Hydroalkylation of Racemic Allylic Alcohols for the Synthesis of Chiral Amino Acid Derivatives. (27th April 2022)

• Record Type: Journal Article
• Authors: Zhang, Xiaohui; Ma, Wei; Zhang, Jinyu; Tang, Weijun; Xue, Dong; Xiao, Jianliang; Sun, Huaming; Wang, Chao
• Is Part Of: Angewandte Chemie. Volume 134:Number 26(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-04-27
• Subjects: Allylic Alcohol -- Amino Acid -- Borrowing Hydrogen -- Dynamic Kinetic Asymmetric Transformation -- Hydroalkylation; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202203244
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: The asymmetric hydroalkylation of racemic allylic alcohols has been developed for the synthesis of chiral amino acid derivatives with two remote chiral centers by borrowing hydrogen catalysis. The stereoselectivities are controlled by a single chiral Ru catalyst via a dynamic kinetic asymmetric transformation process and an interesting diastereoselectivity amplification process of the product. The method could be used for the synthesis of several types of biologically important molecules, including stereodivergent synthesis of chiral pyrrolidine derivatives. Abstract : Racemic allylic alcohols are converted into chiral amino acid derivatives via asymmetric hydroalkylation enabled by borrowing hydrogen catalysis. Mechanistic studies suggested that a single ruthenium chiral catalyst controls the stereoselectivity of two remote chiral centers through a dynamic kinetic asymmetric transformation and a diastereoselectivity amplification process of the product.