Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis

Tomer M. Faraggi; Caroline Rouget-Virbel; Juan A. Rincón; Mario Barberis; Carlos Mateos; Susana García-Cerrada; Javier Agejas; Oscar De Frutos; David W.C. Macmillan

doi:10.1021/acs.oprd.1c00208

Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis

Tomer M. Faraggi, Caroline Rouget-Virbel, Juan A. Rincón, Mario Barberis, Carlos Mateos, Susana García-Cerrada, Javier Agejas, Oscar De Frutos, David W.C. Macmillan

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

33 Scopus citations

Abstract

We describe herein a two-step process for the conversion of serine to a wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial analogues of phenylalanine, tryptophan, and histidine. The reaction is tolerant of a broad range of functionalities and can be leveraged toward the scalable synthesis of valuable pharmaceutical scaffolds via flow technology.

Original language	English (US)
Pages (from-to)	1966-1973
Number of pages	8
Journal	Organic Process Research and Development
Volume	25
Issue number	8
DOIs	https://doi.org/10.1021/acs.oprd.1c00208
State	Published - Aug 20 2021

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Organic Chemistry

Keywords

flow chemistry
heterocycles
nickel catalysis
photoredox catalysis
unnatural amino acids

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10.1021/acs.oprd.1c00208

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title = "Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis",

abstract = "We describe herein a two-step process for the conversion of serine to a wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial analogues of phenylalanine, tryptophan, and histidine. The reaction is tolerant of a broad range of functionalities and can be leveraged toward the scalable synthesis of valuable pharmaceutical scaffolds via flow technology.",

keywords = "flow chemistry, heterocycles, nickel catalysis, photoredox catalysis, unnatural amino acids",

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doi = "10.1021/acs.oprd.1c00208",

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T1 - Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis

AU - Faraggi, Tomer M.

AU - Rouget-Virbel, Caroline

AU - Rincón, Juan A.

AU - Barberis, Mario

AU - Mateos, Carlos

AU - García-Cerrada, Susana

AU - Agejas, Javier

AU - De Frutos, Oscar

AU - Macmillan, David W.C.

PY - 2021/8/20

Y1 - 2021/8/20

N2 - We describe herein a two-step process for the conversion of serine to a wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial analogues of phenylalanine, tryptophan, and histidine. The reaction is tolerant of a broad range of functionalities and can be leveraged toward the scalable synthesis of valuable pharmaceutical scaffolds via flow technology.

AB - We describe herein a two-step process for the conversion of serine to a wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial analogues of phenylalanine, tryptophan, and histidine. The reaction is tolerant of a broad range of functionalities and can be leveraged toward the scalable synthesis of valuable pharmaceutical scaffolds via flow technology.

KW - flow chemistry

KW - heterocycles

KW - nickel catalysis

KW - photoredox catalysis

KW - unnatural amino acids

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AN - SCOPUS:85112556559

SN - 1083-6160

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SP - 1966

EP - 1973

JO - Organic Process Research and Development

JF - Organic Process Research and Development

IS - 8

ER -

Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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