Stereocontrolled Addition of Scrambling ortho-Sulfinyl Carbanions: Easy Access to Homopropargylamines and α-Allenylamines
Entity
UAM. Departamento de QuímicaPublisher
American Chemistry SocietyDate
2020-03-20Citation
10.1021/acs.orglett.0c00625
Organic Letters 22.6 (2020): 2431-2436
ISSN
1523-7060 (print); 1523-7052 (online)DOI
10.1021/acs.orglett.0c00625Funded by
We thank DGAPA-UNAM (Project No. PAPIIT-IN205319) for financial support. B.C.D. thanks CONACYT for a graduate fellowship (Grant No. 335839) and R.I.R. thanks Fundación Carolina for a graduate fellowship. We also thank M. C. García González, R. Gaviño, R. Patiño, M. A. Peña, and R. A. Toscano for their technical assistance (all from UNAM). We are grateful to the Spanish Government (No. RTI2018-095038-B-I00), “Comunidad de Madrid” and European Structural Funds (No. S2018/NMT-4367)Project
Gobierno de España. RTI2018-095038-B-I00; Comunidad de Madrid. S2018/NMT-4367Editor's Version
https://doi.org/10.1021/acs.orglett.0c00625Subjects
Chemical reactions; Aromatic compounds; Electrophiles; Amines; Stereoselectivity; QuímicaNote
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see: https://pubs.acs.org/doi/abs/10.1021/acs.orglett.0c00625Rights
© 2020 American Chemical SocietyAbstract
An unprecedented behavior of ortho-sulfinylpropargyl carbanions in the presence of optically active sulfinylimines affords two different families of compounds: this peculiar chemodivergency is importantly affected by the nature of the employed base, and assisted by the configuration of the electrophile, displaying no alteration in the stereocontrol of both reactions. α-Allenylamines are formed exclusively, using R-sulfinyl aldimines as electrophiles, while homopropargylamines result when S-sulfinyl aldimines are employed.
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Google Scholar:Cruz-Delgado, Balú
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Rodríguez, Ricardo I.
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Rosado-Abón, Anielka
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Sánchez-Obregón, Rubén
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Yuste, Francisco
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Alemán Lara, José Julián
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