Chen Yi-Hung, McDonald Frank E
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
J Am Chem Soc. 2006 Apr 12;128(14):4568-9. doi: 10.1021/ja061082f.
Compounds 1 and 2 are novel synthons for bispropionate synthesis, undergoing stereospecific Lewis acid-catalyzed transfer of the bispropionate unit with a variety of aldehydes, including alpha-chiral aldehydes. Thus 1 leads to the E-alkene bispropionate 3 with anti-stereochemistry, whereas diastereomer 2 gives the Z-alkene product 4, under mild conditions and with complete stereospecificity. The efficacy of this methodology is demonstrated in a short synthesis of invictolide beginning with 2 and (R)-2-methylpentanal.
化合物1和2是用于双丙酸酯合成的新型合成子，可在立体专一性的路易斯酸催化下，与包括α-手性醛在内的多种醛进行双丙酸酯单元的转移。因此，在温和条件下且具有完全的立体专一性时，1可生成具有反式立体化学结构的E-烯烃双丙酸酯3，而2的非对映异构体则生成Z-烯烃产物4。从2和(R)-2-甲基戊醛开始，通过简短的合成过程证明了该方法的有效性。
