The resolution of trans-2,2-dichloro-3-methylcyclopropanecarboxylic acid via crystallization of its salts with (+)- and (−)-α-phenylethylamine, and the transformation of the resulting enantiomers into (R)- and (S)-dimethyl 2-methylsuccinates-Science-Chemical Encyclopedia-lookchem

The resolution of trans-2,2-dichloro-3-methylcyclopropanecarboxylic acid via crystallization of its salts with (+)- and (−)-α-phenylethylamine, and the transformation of the resulting enantiomers into (R)- and (S)-dimethyl 2-methylsuccinates
Add time:07/17/2019 Source:sciencedirect.com

The resolution of trans-2,2-dichloro-3-methylcyclopropanecarboxylic acid trans-1 was achieved by crystallization of its salts with (+)- and (−)-α-phenylethylamine. The chiral acids were converted into methyl esters 9, which upon reaction with sodium methoxide in methanol underwent a three-carbon ring cleavage, leading to the corresponding mono-orthoester derivatives 10. Acidic hydrolysis then gave the known (R)- and (S)-dimethyl 2-methylsuccinates 12.

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