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Asymmetric C–C Bond Formation between Chiral N ‐Phosphonyl Imines and a Nickel(II)‐Complexed Glycine Schiff Base Provides Efficient Synthesis of α,β‐ syn ‐Diamino Acid Derivatives
Author(s) -
Sun Hao,
Zhang Haowei,
Han Jianlin,
Pan Yi,
Li Guigen
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300554
Subject(s) - chemistry , schiff base , vicinal , glycine , stereochemistry , nickel , imine , enantioselective synthesis , medicinal chemistry , amino acid , catalysis , organic chemistry , biochemistry
The group‐assisted purification asymmetric synthesis of α,β‐diamino acid derivatives was achieved by treating chiral N ‐phosphonyl imines with a Ni II ‐complexed glycine‐derived enolate; traditional purification techniques such as chromatography and recrystallization are not required. Successful control of the syn stereochemistry of the vicinal diamino products complements our previous methods that afforded anti stereoisomers; thus, all four individual isomers can be synthesized simply by changing the geometry of the enolate. In contrast to our previous synthesis in which at least 5 equiv. of the glycine Schiff base enolate was required for complete conversion, the new synthesis only needs 1.1 equiv. of the glycine Schiff base enolate to give complete diastereoselectivity (>30:1 dr ) and high yields (91–97 %). The absolute stereochemistry was unambiguously determined by X‐ray structure analysis.