A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling

Shengyang Ni, Alberto F. Garrido-Castro, Rohan R. Merchant, Justine N. de Gruyter, Daniel C. Schmitt, James J. Mousseau, Gary M. Gallego, Shouliang Yang, Michael R. Collins, Jennifer X. Qiao, Kap Sun Yeung, David R. Langley, Michael A. Poss, Paul M. Scola, Tian Qin, Phil S. Baran

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

The direct union of primary, secondary, and tertiary carboxylic acids with a chiral glyoxylate-derived sulfinimine provides rapid access into a variety of enantiomerically pure α-amino acids (>85 examples). Characterized by operational simplicity, this radical-based reaction enables the modular assembly of exotic α-amino acids, including both unprecedented structures and those of established industrial value. The described method performs well in high-throughput library synthesis, and has already been implemented in three distinct medicinal chemistry campaigns.

Original languageEnglish (US)
Pages (from-to)14560-14565
Number of pages6
JournalAngewandte Chemie - International Edition
Volume57
Issue number44
DOIs
StatePublished - Oct 26 2018
Externally publishedYes

Fingerprint

Amino acids
Amino Acids
Carboxylic Acids
Carboxylic acids
Throughput
Pharmaceutical Chemistry
sulfinimine
glyoxylic acid

Keywords

  • amino acid synthesis
  • decarboxylative radical addition
  • library synthesis
  • redox-active esters
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Ni, S., Garrido-Castro, A. F., Merchant, R. R., de Gruyter, J. N., Schmitt, D. C., Mousseau, J. J., ... Baran, P. S. (2018). A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling. Angewandte Chemie - International Edition, 57(44), 14560-14565. https://doi.org/10.1002/anie.201809310

A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling. / Ni, Shengyang; Garrido-Castro, Alberto F.; Merchant, Rohan R.; de Gruyter, Justine N.; Schmitt, Daniel C.; Mousseau, James J.; Gallego, Gary M.; Yang, Shouliang; Collins, Michael R.; Qiao, Jennifer X.; Yeung, Kap Sun; Langley, David R.; Poss, Michael A.; Scola, Paul M.; Qin, Tian; Baran, Phil S.

In: Angewandte Chemie - International Edition, Vol. 57, No. 44, 26.10.2018, p. 14560-14565.

Research output: Contribution to journalArticle

Ni, S, Garrido-Castro, AF, Merchant, RR, de Gruyter, JN, Schmitt, DC, Mousseau, JJ, Gallego, GM, Yang, S, Collins, MR, Qiao, JX, Yeung, KS, Langley, DR, Poss, MA, Scola, PM, Qin, T & Baran, PS 2018, 'A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling', Angewandte Chemie - International Edition, vol. 57, no. 44, pp. 14560-14565. https://doi.org/10.1002/anie.201809310
Ni S, Garrido-Castro AF, Merchant RR, de Gruyter JN, Schmitt DC, Mousseau JJ et al. A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling. Angewandte Chemie - International Edition. 2018 Oct 26;57(44):14560-14565. https://doi.org/10.1002/anie.201809310
Ni, Shengyang ; Garrido-Castro, Alberto F. ; Merchant, Rohan R. ; de Gruyter, Justine N. ; Schmitt, Daniel C. ; Mousseau, James J. ; Gallego, Gary M. ; Yang, Shouliang ; Collins, Michael R. ; Qiao, Jennifer X. ; Yeung, Kap Sun ; Langley, David R. ; Poss, Michael A. ; Scola, Paul M. ; Qin, Tian ; Baran, Phil S. / A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling. In: Angewandte Chemie - International Edition. 2018 ; Vol. 57, No. 44. pp. 14560-14565.
@article{9c8212272aa34ba8bba25855a934aeb9,
title = "A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling",
abstract = "The direct union of primary, secondary, and tertiary carboxylic acids with a chiral glyoxylate-derived sulfinimine provides rapid access into a variety of enantiomerically pure α-amino acids (>85 examples). Characterized by operational simplicity, this radical-based reaction enables the modular assembly of exotic α-amino acids, including both unprecedented structures and those of established industrial value. The described method performs well in high-throughput library synthesis, and has already been implemented in three distinct medicinal chemistry campaigns.",
keywords = "amino acid synthesis, decarboxylative radical addition, library synthesis, redox-active esters, synthetic methods",
author = "Shengyang Ni and Garrido-Castro, {Alberto F.} and Merchant, {Rohan R.} and {de Gruyter}, {Justine N.} and Schmitt, {Daniel C.} and Mousseau, {James J.} and Gallego, {Gary M.} and Shouliang Yang and Collins, {Michael R.} and Qiao, {Jennifer X.} and Yeung, {Kap Sun} and Langley, {David R.} and Poss, {Michael A.} and Scola, {Paul M.} and Tian Qin and Baran, {Phil S.}",
year = "2018",
month = "10",
day = "26",
doi = "10.1002/anie.201809310",
language = "English (US)",
volume = "57",
pages = "14560--14565",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "44",

}

TY - JOUR

T1 - A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling

AU - Ni, Shengyang

AU - Garrido-Castro, Alberto F.

AU - Merchant, Rohan R.

AU - de Gruyter, Justine N.

AU - Schmitt, Daniel C.

AU - Mousseau, James J.

AU - Gallego, Gary M.

AU - Yang, Shouliang

AU - Collins, Michael R.

AU - Qiao, Jennifer X.

AU - Yeung, Kap Sun

AU - Langley, David R.

AU - Poss, Michael A.

AU - Scola, Paul M.

AU - Qin, Tian

AU - Baran, Phil S.

PY - 2018/10/26

Y1 - 2018/10/26

N2 - The direct union of primary, secondary, and tertiary carboxylic acids with a chiral glyoxylate-derived sulfinimine provides rapid access into a variety of enantiomerically pure α-amino acids (>85 examples). Characterized by operational simplicity, this radical-based reaction enables the modular assembly of exotic α-amino acids, including both unprecedented structures and those of established industrial value. The described method performs well in high-throughput library synthesis, and has already been implemented in three distinct medicinal chemistry campaigns.

AB - The direct union of primary, secondary, and tertiary carboxylic acids with a chiral glyoxylate-derived sulfinimine provides rapid access into a variety of enantiomerically pure α-amino acids (>85 examples). Characterized by operational simplicity, this radical-based reaction enables the modular assembly of exotic α-amino acids, including both unprecedented structures and those of established industrial value. The described method performs well in high-throughput library synthesis, and has already been implemented in three distinct medicinal chemistry campaigns.

KW - amino acid synthesis

KW - decarboxylative radical addition

KW - library synthesis

KW - redox-active esters

KW - synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=85055021752&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85055021752&partnerID=8YFLogxK

U2 - 10.1002/anie.201809310

DO - 10.1002/anie.201809310

M3 - Article

C2 - 30212610

AN - SCOPUS:85055021752

VL - 57

SP - 14560

EP - 14565

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 44

ER -