Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 37, Pages 5901-5916Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202000608
Keywords
Condensation reactions; Diastereoselectivity; Ketimine; Reduction; Sulfinamides
Categories
Funding
- CNRS
- Universite Grenoble Alpes
- Nigerian government
- Labex ARCANE
- CBH-EUR-GS [ANR-17-EURE-003]
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Chiral sulfinamides are very valuable, commercially available, and easy to handle chiral auxiliaries. One of the most interesting transformations that can be performed with a chiral sulfinamide is its condensation onto a ketone to form a chiral sulfinylketimine, followed by a reduction to obtain an alpha-chiral primary amine. We review here all the methodologies developed around this condensation/reduction transformation. In the second part, we survey applications of these newly developed methodologies for the synthesis of valuable biologically active compounds, including multikilogram scale synthesis.
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