通过串联 Friedel-Crafts 共轭加成/不对称质子化反应对色氨酸衍生物进行对映选择性合成。
Enantioselective synthesis of tryptophan derivatives by a tandem Friedel-Crafts conjugate addition/asymmetric protonation reaction.
机构信息
The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
出版信息
J Am Chem Soc. 2012 Mar 21;134(11):5131-7. doi: 10.1021/ja209390d. Epub 2012 Mar 5.
Abstract
The tandem Friedel-Crafts conjugate addition/asymmetric protonation reaction between 2-substituted indoles and methyl 2-acetamidoacrylate is reported. The reaction is catalyzed by (R)-3,3'-dibromo-BINOL in the presence of stoichiometric SnCl(4), and is the first example of a tandem conjugate addition/asymmetric protonation reaction using a BINOL·SnCl(4) complex as the catalyst. A range of indoles furnished synthetic tryptophan derivatives in good yields and high levels of enantioselectivity, even on a preparative scale. The convergent nature of this transformation should lend itself to the preparation of unnatural tryptophan derivatives for use in a broad array of synthetic and biological applications.
摘要
报道了 2-取代吲哚与甲基 2-乙酰氨基丙烯酸酯之间的串联 Friedel-Crafts 共轭加成/不对称质子化反应。该反应在等摩尔 SnCl(4)存在下，由(R)-3,3'-二溴-BINOL 催化，是首例使用 BINOL·SnCl(4)配合物作为催化剂的串联共轭加成/不对称质子化反应。一系列吲哚以良好的收率和高对映选择性得到了合成色氨酸衍生物，甚至在制备规模上也是如此。这种转化的收敛性质应该适合于制备用于广泛的合成和生物应用的非天然色氨酸衍生物。
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Enantioselective synthesis of tryptophan derivatives by a tandem Friedel-Crafts conjugate addition/asymmetric protonation reaction.通过串联 Friedel-Crafts 共轭加成/不对称质子化反应对色氨酸衍生物进行对映选择性合成。
J Am Chem Soc. 2012 Mar 21;134(11):5131-7. doi: 10.1021/ja209390d. Epub 2012 Mar 5.
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