Ethyl with TBPS group

Ethyl L-lactate can be protected with a TBPS group by reaction with rer -butyldiphenylsilyl chloride and imidazole in either tetrahydrofuran [134] or DMF [135]. Alternatively, using DBU as the base in methylene chloride furnishes 427 in 100% yield [140]. 

Epoxide 303 has been used an an enantioselective synthesis of the methylenecyclopropa-neacetic acid (514a) portion of (methylenecyclopropyl)acetyl-CoA (514b), a mammalian metabolite of hypoglycines A and B. Addition of the anion derived from phenyl 2-(tri-methylsilyl)ethyl sulfone to 303 produces a 3 1 mixture of threo and erythro diastereomers 509. Either diastereomer cyclizes to the same cyclopropane 511 upon treatment with LDA, which suggests that epimerization at C-5 must be occurring prior to cyclization. Selective removal of the TBPS group followed by oxidation of the alcohol to an acid and elimination affords the desired product 514a (Scheme 73) [126,127]. 

Amino acids (AA), as one of the most abundant biomaterials in nature, are known to be nontoxic, biodegradable, and biocompatible. They are excellent feedstocks for the synthesis of ILs, because of their reasonable cost and environment-friendly characteristics. In 2005, a group of amino acid ionic liquids (AAILs) was first synthesized by Fukumoto s group from 20 natural AA [85]. They prepared AAILs based on l-ethyl-3-methylimidazolium cation, [emim], by neutralization method. In this method, [emim]OH was prepared by anion exchange resin, followed by addition of [emim]OH to a slight excess of an equimolar AA aqueous solution to prepare salts and water as a by-product [86]. Further, they synthesized tetrabutylphosphonium-based AAILs ([TBP][AA]) by mixing AA with aqueous solution of tetrabutylphosphonium hydroxide ([TBP][OH]) [87]. Tao et al. [88] synthesized [AAE]N03 ILs ([AAE] stands for AA ester as cation and NO3 stands... 

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