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...

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Vydáno v:	Chemistry : a European journal Ročník 20; číslo 26; s. 7926 - 7930
Hlavní autoři:	Xin, Zhuo, Kramer, Søren, Overgaard, Jacob, Skrydstrup, Troels
Médium:	Journal Article
Jazyk:	angličtina
Vydáno:	Weinheim WILEY-VCH Verlag 23.06.2014 WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc
Témata:	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
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Popis
Shrnutí:	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).
Bibliografie:	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