Small Change, Big Impact: Reversal of Diastereoselection in Cuprate Conjugate Additions to α,β-Unsaturated Lactams and Identification of a Competing Mechanism-Reference-Cited by-同舟云学术

Small Change, Big Impact: Reversal of Diastereoselection in Cuprate Conjugate Additions to α,β-Unsaturated Lactams and Identification of a Competing Mechanism

Published:2023-03-20 Issue:7 Volume:88 Page:4387-4396
ISSN:0022-3263
Container-title:The Journal of Organic Chemistry
language:en
Short-container-title:J. Org. Chem.

Author:

Wright Stephen W.¹^ORCID,Choi Chulho¹^ORCID,Kawamata Yu²^ORCID,Baran Phil S.²^ORCID

Affiliation:

1. Medicine Design, Pfizer Global Research and Development, 445 Eastern Point Road, Groton, Connecticut 06340, United States

2. Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/acs.joc.2c02993

Reference34 articles.

1. Reversal of Diastereoselection in the Conjugate Addition of Cuprates to Unsaturated Lactams

2. Stereoselective synthesis of protected (2S,3S)-N-methyl-5-hydroxyisoleucine, a component of halipeptins

3. Total Synthesis of Salinosporamide A

4. Discovery of Clinical Candidate 1-{[(2S,3S,4S)-3-Ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy}-7-methoxyisoquinoline-6-carboxamide (PF-06650833), a Potent, Selective Inhibitor of Interleukin-1 Receptor Associated Kinase 4 (IRAK4), by Fragment-Based Drug Design

5. Improvements to Enable the Large Scale Synthesis of 1-{[(2S,3S,4S)-3-Ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy}-7-methoxyisoquinoline-6-carboxamide (PF-06650833)

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