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Asymmetric C-C Bond Formation between Chiral N-Phosphonyl Imines and Ni(II)-Complex of Glycine Schiff Base Provides a GAP Synthesis of ?,?-syn-Diamino Acid Derivatives.

ABSTRACT: The GAP asymmetric synthesis of ?,?-diamino acid derivatives has been achieved by reacting chiral N-phosphonyl imines with Ni(II)-complex of glycine ester-based enolate without the use of traditional purifications of chromatography and recrystallization. The successful control of synstereochemistry of vicinal diamino products complements our previous methods which afforded anti stereoisomers and enables all four individual isomers to be synthesized by simply changing enolate geometry. In contrast to our previous synthesis where required at least 5 equiv of glycine Schiff base enolate for complete conversion, the new synthesis only needs 1.1 equiv of glycine Schiff base enolate to give complete diastereoselectivity (>99% de) and yields (91% - 97%). The absolute stereochemistry has been unambiguously determined by X-ray structural analysis.

SUBMITTER: Sun H 

PROVIDER: S-EPMC4192728 | biostudies-literature | 2013 Aug

REPOSITORIES: biostudies-literature

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Asymmetric C-C Bond Formation between Chiral <i>N</i>-Phosphonyl Imines and Ni(II)-Complex of Glycine Schiff Base Provides a GAP Synthesis of α,β-<i>syn</i>-Diamino Acid Derivatives.

Sun Hao H   Zhang Haowei H   Han Jianlin J   Pan Yi Y   Li Guigen G  

European journal of organic chemistry 20130801 22

The GAP asymmetric synthesis of α,β-diamino acid derivatives has been achieved by reacting chiral N-phosphonyl imines with Ni(II)-complex of glycine ester-based enolate without the use of traditional purifications of chromatography and recrystallization. The successful control of synstereochemistry of vicinal diamino products complements our previous methods which afforded anti stereoisomers and enables all four individual isomers to be synthesized by simply changing enolate geometry. In contras  ...[more]

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