Stereoselective synthesis of chiral thiol-containing 1,2-aminoalcohols via SmI 2 -mediated coupling
Tetrahedron, ISSN: 0040-4020, Vol: 76, Issue: 51, Page: 131249
2020
- 7Citations
- 6Captures
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Article Description
The stereoselective synthesis of highly functionalized aminohydroxythiols represents a synthetic challenge as the oxidation sensitivity and coordinating property of the thiol group interferes with many established synthetic methods. The SmI 2 /LiBr-mediated reductive coupling between Ellman N -sulfinylimines, containing thiol groups protected either as trityl thioether or dihydrothiazolidine, and aldehydes enables the synthesis of chiral aminohydroxythiols in high enantio- and diastereoselectivity. The scope of this reaction has been established for 18 examples and applied for the synthesis of a complex intermediate needed for a biosynthesis study.
Bibliographic Details
http://www.sciencedirect.com/science/article/pii/S0040402020303926; http://dx.doi.org/10.1016/j.tet.2020.131249; http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=85084410754&origin=inward; https://linkinghub.elsevier.com/retrieve/pii/S0040402020303926; https://dx.doi.org/10.1016/j.tet.2020.131249
Elsevier BV
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