Synthesis of 1-benzylisoindoline and 1-benzyl-tetrahydroisoquinoline through nucleophilic addition of organozinc reagents to N , O -acetals

A new approach to access 1-benzylisoindoline and 1-benzyl-tetrahydroisoquinoline has been developed through nucleophilic addition of organozinc reagents to N,O-acetals. A number of substituted organozinc reagents were amenable for this transformation, and the desired products were obtained with exce...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-09, Vol.18 (36), p.7139-7150
Main Authors: Ma, Rui-Jun, Sun, Jian-Ting, Liu, Chang-Hong, Chen, Ling, Si, Chang-Mei, Wei, Bang-Guo
Format: Article
Language:English
Subjects:
Acetals
Catalysts
Crystallography
Reagents
Tetrahydroisoquinoline
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A new approach to access 1-benzylisoindoline and 1-benzyl-tetrahydroisoquinoline has been developed through nucleophilic addition of organozinc reagents to N,O-acetals. A number of substituted organozinc reagents were amenable for this transformation, and the desired products were obtained with excellent yields. Moreover, Sc(OTf)3 proved to be an effective catalyst for the formation of 1-benzylisoindoline and 1-benzyl-tetrahydroisoquinoline using such nucleophilic addition.
ISSN:1477-0520
1477-0539
DOI:10.1039/D0OB01477J