Asymmetric Synthesis of Chiral alpha-Methyl-alpha,beta-diamino Acid Derivatives via Group-Assisted Purification Chemistry Using N-Phosphonyl Imines and a Ni(II)-Complexed Alanine Schiff Base

Haowei Zhang, Bing Yang, Zhen Yang, Hongjian Lu, Guigen Li

Research output: Contribution to journalArticle

Abstract

The Mannich reaction between chiral N-phosphonyl imines and a Ni(II)-complexed alanine Schiff base (Ala-Ni) is reported. With a chiral phosphonyl auxiliary, a single isomer of alpha-methyl-alpha,beta-diamino acid derivative containing vicinal chiral centers, including a chiral quaternary carbon center, can be obtained simply by washing the crude mixture with cosolvents. The absolute stereochemistry of the enantiomerically pure product has been unambiguously determined by X-ray crystallographic analysis.
Original languageEnglish
Pages (from-to)7654-7661
JournalJournal of Organic Chemistry
StatePublished - Sep 2016

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