Access to 1,2-Dihydroisoquinolines through Gold-Catalyzed Formal [4+2] Cycloaddition

A new synthetic route to the privileged 1,2‐dihydroisoquinolines is reported. This method, which relies on a gold‐catalyzed formal [4+2] cycloaddition between ynamides and imines, provides a new retrosynthetic disconnection of the 1,2‐dihydroisoquinoline core by installing the 1,8a CC and 2,3 CN b...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal Vol. 20; no. 26; pp. 7926 - 7930
Main Authors: Xin, Zhuo, Kramer, Søren, Overgaard, Jacob, Skrydstrup, Troels
Format: Journal Article
Language:English
Published: Weinheim WILEY-VCH Verlag 23.06.2014
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
Subjects:
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cyclization
Cycloaddition
Cycloaddition Reaction
Disengaging
Gold
Gold - chemistry
heterocycles
homogeneous catalysis
Imines
Isoquinolines - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
Synthesis
ynamides
IMINES
EFFICIENT SYNTHESIS
HYDROAMINATION
ALKYNES
ALPHA,BETA-UNSATURATED AMIDINES
gold
cycloaddition
TETRAHYDROISOQUINOLINE ANTITUMOR ANTIBIOTICS
homogeneous catalysis
heterocycles
MANNICH REACTIONS
BIFUNCTIONAL CATALYST
ynamides
TANDEM NUCLEOPHILIC-ADDITION
CONCISE SYNTHESIS
ISSN:0947-6539, 1521-3765
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A new synthetic route to the privileged 1,2‐dihydroisoquinolines is reported. This method, which relies on a gold‐catalyzed formal [4+2] cycloaddition between ynamides and imines, provides a new retrosynthetic disconnection of the 1,2‐dihydroisoquinoline core by installing the 1,8a CC and 2,3 CN bonds in one step. Both aldimines and ketimines can be used as substrates. In addition, one example of dihydrofuropyridine synthesis is also demonstrated. Heterocycles: A new synthetic route to the privileged 1,2‐dihydroisoquinolines is reported. This method, which relies on a gold‐catalyzed formal [4+2] cycloaddition between ynamides and imines, provides a new retrosynthetic disconnection of the 1,2‐dihydroisoquinoline core by installing the 1,8a CC and 2,3 CN bonds in one step. Both aldimines and ketimines can be used as substrates. In addition, one example of dihydrofuropyridine synthesis is also demonstrated (see scheme).
Bibliography:China Scholarship Council
istex:1A833E0920E44ED796D95C06113A73EFAE3DC7CA
Carlsberg Foundation
Danish National Research Foundation - No. DNRF59
ArticleID:CHEM201403290
Aarhus University
ark:/67375/WNG-TK2WW51W-5
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
content type line 23
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201403290