Diastereoselective synthesis of a highly functionalized angularly substituted cis-perhydroisoquinoline-3,6-dione via organoiron

Jeng-Liang Han; Meng-Chi Liu; Chi Wi Ong

doi:10.1021/jo902605w

Diastereoselective synthesis of a highly functionalized angularly substituted cis-perhydroisoquinoline-3,6-dione via organoiron

J Org Chem. 2010 Mar 5;75(5):1637-42. doi: 10.1021/jo902605w.

Authors

Jeng-Liang Han¹, Meng-Chi Liu, Chi Wi Ong

Affiliation

¹ Department of Chemistry, National Sun Yat Sen University, Kaohsiung, Taiwan 804.

PMID: 20112972
DOI: 10.1021/jo902605w

Abstract

Nitrile addition to cyclohexadienyium-Fe(CO)(3) perchlorate salt provides an efficient entry into the angularly substituted cis-fused perhydroisoquinoline ring system. The key steps in the assembly of the angularly substituted cis-octahydroisoquinoline ring are the transformation of the nitrile to an N-(benzylmethylencie)amino group and a diastereoselective intramolecular Michael reaction to form the bicyclic ring.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds / chemical synthesis*
Bridged Bicyclo Compounds / chemistry
Hydrogenation
Iron Compounds / chemistry*
Isoquinolines / chemical synthesis*
Isoquinolines / chemistry
Models, Molecular
Molecular Structure
Nitriles / chemistry*
Stereoisomerism

Substances

Bridged Bicyclo Compounds
Iron Compounds
Isoquinolines
Nitriles
cis-perhydroisoquinoline-3,6-dione