Organocatalytic Atroposelective Synthesis of Isoquinolines via Dynamic Kinetic Resolution

Ahreum Kim; Junsoo Moon; Chanhee Lee; Jayoung Song; Jongchan Kim; Yongseok Kwon

doi:10.1021/acs.orglett.1c04330

Organocatalytic Atroposelective Synthesis of Isoquinolines via Dynamic Kinetic Resolution

Ahreum Kim, Junsoo Moon, Chanhee Lee, Jayoung Song, Jongchan Kim, Yongseok Kwon

Department of Pharmacy

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

10 Scopus citations

Abstract

Herein, a highly enantioselective Pictet-Spengler reaction for the synthesis of axially chiral tetrahydroisoquinolines via dynamic kinetic resolution is described. Chiral phosphoric acids catalyze cyclization to yield single regioisomeric isoquinolines with excellent enantioselectivities around the C-C bond up to 99% ee. The current protocol is effective for a wide range of substrates, and the observed enantiodivergence depends on the substituents on the catalysts.

Original language	English
Pages (from-to)	1077-1082
Number of pages	6
Journal	Organic Letters
Volume	24
Issue number	4
DOIs	https://doi.org/10.1021/acs.orglett.1c04330
State	Published - 4 Feb 2022

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10.1021/acs.orglett.1c04330

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title = "Organocatalytic Atroposelective Synthesis of Isoquinolines via Dynamic Kinetic Resolution",

abstract = "Herein, a highly enantioselective Pictet-Spengler reaction for the synthesis of axially chiral tetrahydroisoquinolines via dynamic kinetic resolution is described. Chiral phosphoric acids catalyze cyclization to yield single regioisomeric isoquinolines with excellent enantioselectivities around the C-C bond up to 99\% ee. The current protocol is effective for a wide range of substrates, and the observed enantiodivergence depends on the substituents on the catalysts.",

author = "Ahreum Kim and Junsoo Moon and Chanhee Lee and Jayoung Song and Jongchan Kim and Yongseok Kwon",

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doi = "10.1021/acs.orglett.1c04330",

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TY - JOUR

T1 - Organocatalytic Atroposelective Synthesis of Isoquinolines via Dynamic Kinetic Resolution

AU - Kim, Ahreum

AU - Moon, Junsoo

AU - Lee, Chanhee

AU - Song, Jayoung

AU - Kim, Jongchan

AU - Kwon, Yongseok

PY - 2022/2/4

Y1 - 2022/2/4

N2 - Herein, a highly enantioselective Pictet-Spengler reaction for the synthesis of axially chiral tetrahydroisoquinolines via dynamic kinetic resolution is described. Chiral phosphoric acids catalyze cyclization to yield single regioisomeric isoquinolines with excellent enantioselectivities around the C-C bond up to 99% ee. The current protocol is effective for a wide range of substrates, and the observed enantiodivergence depends on the substituents on the catalysts.

AB - Herein, a highly enantioselective Pictet-Spengler reaction for the synthesis of axially chiral tetrahydroisoquinolines via dynamic kinetic resolution is described. Chiral phosphoric acids catalyze cyclization to yield single regioisomeric isoquinolines with excellent enantioselectivities around the C-C bond up to 99% ee. The current protocol is effective for a wide range of substrates, and the observed enantiodivergence depends on the substituents on the catalysts.

UR - https://www.scopus.com/pages/publications/85124056700

U2 - 10.1021/acs.orglett.1c04330

DO - 10.1021/acs.orglett.1c04330

M3 - Article

C2 - 35076251

AN - SCOPUS:85124056700

SN - 1523-7060

VL - 24

SP - 1077

EP - 1082

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

Organocatalytic Atroposelective Synthesis of Isoquinolines via Dynamic Kinetic Resolution

Abstract

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