Asymmetric Organocatalysis and Photoredox Catalysis for the α-Functionalization of Tetrahydroisoquinolines

Hong Hou; Shaoqun Zhu; Iuliana Atodiresei; Magnus Rueping

doi:10.1002/ejoc.201800117

Asymmetric Organocatalysis and Photoredox Catalysis for the α-Functionalization of Tetrahydroisoquinolines

Hong Hou, Shaoqun Zhu, Iuliana Atodiresei, Magnus Rueping^*

^*Corresponding author for this work

Chemistry

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

35 Scopus citations

Abstract

The asymmetric α-alkylation of tetrahydroisoquinolines with cyclic ketones has been accomplished in the presence of a combined catalytic system consisting of a visible-light photoredox catalyst and a chiral primary amine organocatalyst. The desired products were obtained in good yields, high enantioselectivity, and good to excellent diastereoselectivity. (PC: photoredox cycle, EN: enamine cycle).

Original language	English (US)
Pages (from-to)	1277-1280
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	10
DOIs	https://doi.org/10.1002/ejoc.201800117
State	Published - Mar 14 2018

Keywords

Alkylation
Cyclic ketones
Organocatalysis
Photocatalysis
Tetrahydroisoquinolines

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201800117

Cite this

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title = "Asymmetric Organocatalysis and Photoredox Catalysis for the α-Functionalization of Tetrahydroisoquinolines",

abstract = "The asymmetric α-alkylation of tetrahydroisoquinolines with cyclic ketones has been accomplished in the presence of a combined catalytic system consisting of a visible-light photoredox catalyst and a chiral primary amine organocatalyst. The desired products were obtained in good yields, high enantioselectivity, and good to excellent diastereoselectivity. (PC: photoredox cycle, EN: enamine cycle).",

keywords = "Alkylation, Cyclic ketones, Organocatalysis, Photocatalysis, Tetrahydroisoquinolines",

author = "Hong Hou and Shaoqun Zhu and Iuliana Atodiresei and Magnus Rueping",

note = "Publisher Copyright: {\textcopyright} 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

month = mar,

day = "14",

doi = "10.1002/ejoc.201800117",

language = "English (US)",

volume = "2018",

pages = "1277--1280",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

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T1 - Asymmetric Organocatalysis and Photoredox Catalysis for the α-Functionalization of Tetrahydroisoquinolines

AU - Hou, Hong

AU - Zhu, Shaoqun

AU - Atodiresei, Iuliana

AU - Rueping, Magnus

PY - 2018/3/14

Y1 - 2018/3/14

N2 - The asymmetric α-alkylation of tetrahydroisoquinolines with cyclic ketones has been accomplished in the presence of a combined catalytic system consisting of a visible-light photoredox catalyst and a chiral primary amine organocatalyst. The desired products were obtained in good yields, high enantioselectivity, and good to excellent diastereoselectivity. (PC: photoredox cycle, EN: enamine cycle).

AB - The asymmetric α-alkylation of tetrahydroisoquinolines with cyclic ketones has been accomplished in the presence of a combined catalytic system consisting of a visible-light photoredox catalyst and a chiral primary amine organocatalyst. The desired products were obtained in good yields, high enantioselectivity, and good to excellent diastereoselectivity. (PC: photoredox cycle, EN: enamine cycle).

KW - Alkylation

KW - Cyclic ketones

KW - Organocatalysis

KW - Photocatalysis

KW - Tetrahydroisoquinolines

UR - http://www.scopus.com/inward/record.url?scp=85043700033&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201800117

DO - 10.1002/ejoc.201800117

M3 - Article

AN - SCOPUS:85043700033

SN - 1434-193X

VL - 2018

SP - 1277

EP - 1280

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 10

ER -

Asymmetric Organocatalysis and Photoredox Catalysis for the α-Functionalization of Tetrahydroisoquinolines

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 1819590: Experimental Crystal Structure Determination : (S)-2-[(R)-2-(4-bromophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl]cyclohexan-1-one

Cite this

Asymmetric Organocatalysis and Photoredox Catalysis for the α-Functionalization of Tetrahydroisoquinolines

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1819590: Experimental Crystal Structure Determination : (S)-2-[(R)-2-(4-bromophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl]cyclohexan-1-one

Cite this