Photoredox Catalytic Installation of an Alkyl/Aryl Side Chain and Deuterium into (S)-Methyleneoxazolidinone: Synthesis of Enantioenriched α-Deuterated α-Amino Acid Derivatives

Yue Dong; Xiang Meng; Giri Gnawali; Mengyang Chang; Wei Wang

doi:10.1021/acs.orglett.3c01760

Photoredox Catalytic Installation of an Alkyl/Aryl Side Chain and Deuterium into (S)-Methyleneoxazolidinone: Synthesis of Enantioenriched α-Deuterated α-Amino Acid Derivatives

Yue Dong
, Xiang Meng
, Giri Gnawali
, Mengyang Chang
, Wei Wang

Pharmacology and Toxicology

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

7 Scopus citations

Abstract

A photoredox catalytic asymmetric method has been established for the installation of both aliphatic and aromatic side chains and the introduction of deuterium into the chiral methyleneoxazolidinone simultaneously. Efficient coupling of readily available boronic acids with the chiral auxiliary delivers structurally diverse α-deuterated α-amino acid derivatives with a high level of diastereoselectivity and deuteration.

Original language	English (US)
Pages (from-to)	4745-4749
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	25
DOIs	https://doi.org/10.1021/acs.orglett.3c01760
State	Published - Jun 30 2023

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Photoredox Catalytic Installation of an Alkyl/Aryl Side Chain and Deuterium into (S)-Methyleneoxazolidinone: Synthesis of Enantioenriched α-Deuterated α-Amino Acid Derivatives",

abstract = "A photoredox catalytic asymmetric method has been established for the installation of both aliphatic and aromatic side chains and the introduction of deuterium into the chiral methyleneoxazolidinone simultaneously. Efficient coupling of readily available boronic acids with the chiral auxiliary delivers structurally diverse α-deuterated α-amino acid derivatives with a high level of diastereoselectivity and deuteration.",

author = "Yue Dong and Xiang Meng and Giri Gnawali and Mengyang Chang and Wei Wang",

note = "Funding Information: Financial support was provided by the National Institutes of Health (Grant 5R01GM125920-03). Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

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day = "30",

doi = "10.1021/acs.orglett.3c01760",

language = "English (US)",

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journal = "Organic Letters",

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T1 - Photoredox Catalytic Installation of an Alkyl/Aryl Side Chain and Deuterium into (S)-Methyleneoxazolidinone

T2 - Synthesis of Enantioenriched α-Deuterated α-Amino Acid Derivatives

AU - Dong, Yue

AU - Meng, Xiang

AU - Gnawali, Giri

AU - Chang, Mengyang

AU - Wang, Wei

PY - 2023/6/30

Y1 - 2023/6/30

N2 - A photoredox catalytic asymmetric method has been established for the installation of both aliphatic and aromatic side chains and the introduction of deuterium into the chiral methyleneoxazolidinone simultaneously. Efficient coupling of readily available boronic acids with the chiral auxiliary delivers structurally diverse α-deuterated α-amino acid derivatives with a high level of diastereoselectivity and deuteration.

AB - A photoredox catalytic asymmetric method has been established for the installation of both aliphatic and aromatic side chains and the introduction of deuterium into the chiral methyleneoxazolidinone simultaneously. Efficient coupling of readily available boronic acids with the chiral auxiliary delivers structurally diverse α-deuterated α-amino acid derivatives with a high level of diastereoselectivity and deuteration.

UR - https://www.scopus.com/pages/publications/85164231848

UR - https://www.scopus.com/pages/publications/85164231848#tab=citedBy

U2 - 10.1021/acs.orglett.3c01760

DO - 10.1021/acs.orglett.3c01760

M3 - Article

C2 - 37326373

AN - SCOPUS:85164231848

SN - 1523-7060

VL - 25

SP - 4745

EP - 4749

JO - Organic Letters

JF - Organic Letters

IS - 25

ER -

Photoredox Catalytic Installation of an Alkyl/Aryl Side Chain and Deuterium into (S)-Methyleneoxazolidinone: Synthesis of Enantioenriched α-Deuterated α-Amino Acid Derivatives

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