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Chemistry of Unsymmetrical Quarternary Carbon Compounds III. Synthesis of (‐)‐Dimethyl 2‐Cyano‐2‐Methylsuccinate and Determination of Its Absolute Configuration
Author(s) -
Lee Kong Ko
Publication year - 1973
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.197300012
Subject(s) - chemistry , absolute configuration , carbon fibers , stereochemistry , medicinal chemistry , organic chemistry , materials science , composite number , composite material
(−)‐Dimethyl 2‐cyano‐2‐methylsuccinate ((−)‐IIIa) was synthesized from menthyl cyanoacetate ((−)‐I), and the absolute configuration of which was elucidated as (S)‐configuration by chemical correlation to the known (R)(+)‐β‐methylterbic acid ((R)(+)‐VII). (−)‐Dimethyl 2‐carbamoyl‐2‐methylsuccinate ((−)‐IV) and (−)‐methyl 3‐methyl‐2,5‐dioxo‐3‐pyrrolidinecarboxylate ((−)‐V) are also confirmed as belonging to (S)‐configuration and (+)‐3‐(1‐hydroxy‐1‐methylethyl)‐3‐methyl‐2,5‐pyrrolidinedione ((+)‐VI) is belonging to (R)‐configuration. Preliminary experiments on racemic compounds are also described.