1,3-二取代四氢异喹啉和顺式或反式异构体以及2,5-二取代吡咯烷的可控合成。

Controlled synthesis of cis or trans isomers of 1,3-disubstituted tetrahydroisoquinolines and 2,5-disubstituted pyrrolidines.

作者信息

Eustache Jacques, Van de Weghe Pierre, Le Nouen Didier, Uyehara Hiroshi, Kabuto Chizuko, Yamamoto Yoshinori

机构信息

Laboratoire de Chimie Organique et Bioorganique associé au CNRS, Université de Haute-Alsace, Ecole Nationale Supérieure de Chimie de Mulhouse, 3, rue Alfred Werner, F-68093 Mulhouse Cedex, France.

出版信息

J Org Chem. 2005 May 13;70(10):4043-53. doi: 10.1021/jo0501543.

DOI:10.1021/jo0501543

PMID:15876095

Abstract

[reactions: see text] The stereoselective outcome of Pd(II)- or Ag(I)-catalyzed intramolecular N-alkylation to afford 1,3-disubstituted 1,2,3,4-tetrahydroisoquinolines was examined. In the absence of additional substituents, Pd(II) allows a facile access to the cis isomers, while Ag(I) favors formation of the trans isomers. The same observation was made for the synthesis of 2,5-disubstituted pyrrolidines. Possible reasons for the observed stereoselectivities are discussed.

摘要

[反应：见正文] 研究了钯（II）或银（I）催化的分子内N-烷基化反应生成1,3-二取代的1,2,3,4-四氢异喹啉的立体选择性结果。在没有额外取代基的情况下，钯（II）能轻松得到顺式异构体，而银（I）则有利于反式异构体的形成。对于2,5-二取代吡咯烷的合成也有相同的观察结果。讨论了观察到的立体选择性的可能原因。