| 摘要 |
<p>organic chemistry, chemical technology. SUBSTANCE: invention relates to the improved method of synthesis of diisopinocampheylchloroborane of the formula (I) in reaction mixture that involves interaction of sodium boron hydride and boron trichloride with alpha-pinene in inert solvent. Synthesized diisopinocampheylchloroborane can be used without isolation for reduction of prochiral ketones to corresponding alcohols of high optical purity. Invention proposes also method of reduction of prochiral ketone of the formula (II) to obtain optically active alcohol of the formula (III) where A is -CH=CH-S- or -CH=CH-CH=CH-; R1 and R2 are hydrogen or halogen atom; R3 is groups CO2R6, COR6, C(R7)2-OR8 where R6 is hydrogen atom or lower alkyl, R7 is lower alkyl and R8 is hydrogen atom or hydroxy-protective group. Alcohol of high optical purity is synthesized by interaction of sodium boron hydride and boron trichloride with alpha-pinene (optical purity of the latter is 70% or above) in inert organic solvent to obtain reaction mixture containing diisopinocampheylchloroborane followed by interaction of obtained mixture with prochiral ketone. The above indicated alpha-pinene is (1R)-(+)-alpha-pinene and solvent is polyalkoxylated ether. EFFECT: improved method of synthesis, high optical purity. 7 cl, 2 ex</p> |
