Asymmetric synthesis of 1-vinyltetrahydroisoquinoline through Pd-catalyzed intramolecular allylic amination

Ce Shi; Iwao Ojima

doi:10.1016/j.tet.2007.04.097

Asymmetric synthesis of 1-vinyltetrahydroisoquinoline through Pd-catalyzed intramolecular allylic amination

Ce Shi
, Iwao Ojima

Chemistry

Stony Brook University

Research output: Contribution to journal › Article › peer-review

47 Scopus citations

Abstract

Asymmetric synthesis of 6,7-dimethoxy-1-vinyltetrahydroisoquinolines through Pd-catalyzed intramolecular allylic amination of 3-(amidoethylphenyl)prop-2-enyl carbonates was studied, using a library of fine-tunable monodentate phosphoramidite ligands. Under optimized conditions, excellent enantiopurity (up to 96% ee) and 100% product selectivity were achieved. 1-Vinyltetrahydroquinoline thus obtained is a highly versatile intermediate for the synthesis of various biologically active alkaloids of medicinal interest.

Original language	English
Pages (from-to)	8563-8570
Number of pages	8
Journal	Tetrahedron
Volume	63
Issue number	35
DOIs	https://doi.org/10.1016/j.tet.2007.04.097
State	Published - Aug 27 2007

Keywords

Alkaloid
Allylic amination
Asymmetric synthesis
Monodentate phosphoramidite
Palladium
Tetrahydroisoquinoline

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10.1016/j.tet.2007.04.097

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title = "Asymmetric synthesis of 1-vinyltetrahydroisoquinoline through Pd-catalyzed intramolecular allylic amination",

abstract = "Asymmetric synthesis of 6,7-dimethoxy-1-vinyltetrahydroisoquinolines through Pd-catalyzed intramolecular allylic amination of 3-(amidoethylphenyl)prop-2-enyl carbonates was studied, using a library of fine-tunable monodentate phosphoramidite ligands. Under optimized conditions, excellent enantiopurity (up to 96\% ee) and 100\% product selectivity were achieved. 1-Vinyltetrahydroquinoline thus obtained is a highly versatile intermediate for the synthesis of various biologically active alkaloids of medicinal interest.",

keywords = "Alkaloid, Allylic amination, Asymmetric synthesis, Monodentate phosphoramidite, Palladium, Tetrahydroisoquinoline",

author = "Ce Shi and Iwao Ojima",

year = "2007",

month = aug,

day = "27",

doi = "10.1016/j.tet.2007.04.097",

language = "English",

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pages = "8563--8570",

journal = "Tetrahedron",

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T1 - Asymmetric synthesis of 1-vinyltetrahydroisoquinoline through Pd-catalyzed intramolecular allylic amination

AU - Shi, Ce

AU - Ojima, Iwao

PY - 2007/8/27

Y1 - 2007/8/27

N2 - Asymmetric synthesis of 6,7-dimethoxy-1-vinyltetrahydroisoquinolines through Pd-catalyzed intramolecular allylic amination of 3-(amidoethylphenyl)prop-2-enyl carbonates was studied, using a library of fine-tunable monodentate phosphoramidite ligands. Under optimized conditions, excellent enantiopurity (up to 96% ee) and 100% product selectivity were achieved. 1-Vinyltetrahydroquinoline thus obtained is a highly versatile intermediate for the synthesis of various biologically active alkaloids of medicinal interest.

AB - Asymmetric synthesis of 6,7-dimethoxy-1-vinyltetrahydroisoquinolines through Pd-catalyzed intramolecular allylic amination of 3-(amidoethylphenyl)prop-2-enyl carbonates was studied, using a library of fine-tunable monodentate phosphoramidite ligands. Under optimized conditions, excellent enantiopurity (up to 96% ee) and 100% product selectivity were achieved. 1-Vinyltetrahydroquinoline thus obtained is a highly versatile intermediate for the synthesis of various biologically active alkaloids of medicinal interest.

KW - Alkaloid

KW - Allylic amination

KW - Asymmetric synthesis

KW - Monodentate phosphoramidite

KW - Palladium

KW - Tetrahydroisoquinoline

UR - https://www.scopus.com/pages/publications/34447520042

U2 - 10.1016/j.tet.2007.04.097

DO - 10.1016/j.tet.2007.04.097

M3 - Article

AN - SCOPUS:34447520042

SN - 0040-4020

VL - 63

SP - 8563

EP - 8570

JO - Tetrahedron

JF - Tetrahedron

IS - 35

ER -

Asymmetric synthesis of 1-vinyltetrahydroisoquinoline through Pd-catalyzed intramolecular allylic amination

Abstract

Keywords

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