1-对甲苯磺酰基-3-乙烯基吲哚的催化不对称重氮乙酸酯环丙烷化反应。一种构建构象受限的高色胺的方法。

Catalytic asymmetric diazoacetate cyclopropanation of 1-tosyl-3-vinylindoles. A route to conformationally restricted homotryptamines.

作者信息

Marcin Lawrence R, Denhart Derek J, Mattson Ronald J

机构信息

Discovery Chemistry, Bristol-Myers Squibb Pharmaceutical Research Institute, Wallingford, Connecticut 06492, USA.

出版信息

Org Lett. 2005 Jun 23;7(13):2651-4. doi: 10.1021/ol050790n.

DOI:10.1021/ol050790n

PMID:15957913

Abstract

[reaction: see text] Substituted 1-tosyl-3-vinylindoles undergo catalytic asymmetric cyclopropanation with ethyl- and tert-butyldiazoacetate to afford N-protected trans-2-(indol-3-yl)-1-cyclopropanecarboxylic esters in good yield and high enantiomeric excess (81-88% ee). The resulting cycloadducts are demonstrated to be useful intermediates for the synthesis of conformationally restricted, homotryptamine-like analogues such as BMS-505130.

摘要

[反应：见正文] 取代的1-对甲苯磺酰基-3-乙烯基吲哚与乙酸乙酯和叔丁基重氮乙酸酯发生催化不对称环丙烷化反应，以良好的产率和高对映体过量（81 - 88% ee）得到N-保护的反式-2-(吲哚-3-基)-1-环丙烷羧酸酯。结果表明，所得的环加成产物是合成构象受限的、类同型色胺类似物（如BMS-505130）的有用中间体。