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

doi:10.1002/anie.201809310

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 journal › Article › peer-review

93 Scopus citations

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 language	English (US)
Pages (from-to)	14560-14565
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	44
DOIs	https://doi.org/10.1002/anie.201809310
State	Published - Oct 26 2018
Externally published	Yes

Keywords

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

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201809310

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Ni, S., Garrido-Castro, A. F., Merchant, R. R., de Gruyter, J. N., Schmitt, D. C., Mousseau, J. J., Gallego, G. M., Yang, S., Collins, M. R., Qiao, J. X., Yeung, K. S., Langley, D. R., Poss, M. A., Scola, P. M., Qin, T., & 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

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

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AU - Schmitt, Daniel C.

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

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