Lithium Hexamethyldisilazide → diisopropyl (2R,3S)-2-(cyclopentylmethyl)-3-hydroxysuccinate

Participants

Reaction Conditions

Reaction Steps

To a cold (5° C.) solution of diisopropyl-(S)-(−)-malate (50.0 g, 229.1 mmol, 1.0 eq.) and (iodomethyl)cyclopentane (55.6 g, 264.6 mmol, 1.15 eq.) in anhydrous THF (250 mL) under N2 was added over a period of 90 min. a solution (1M) of lithium bis(trimethylsilyl)amide (481 mL; 1.0 M, 481.1 mmol, 2.1 eq.) in THF. The temperature was allowed to warm to 20° C. and the mixture was stirred for 15 hours until completion (monitoring by TLC (SiO2); cyclohexane 8-ethyl acetate 2; treated with molibdic acid).

Provenance & Evidence