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Stereoselective Conjugate Addition-Enamination of α-Linear N - tert -Butanesulfinyl Ketimines with Nitroolefins.
- Source :
-
Synthesis . Oct2022, Vol. 54 Issue 19, p4361-4370. 10p. - Publication Year :
- 2022
-
Abstract
- N -Sulfinyl metalloenamines, generated by deprotonating α-linear N - tert -butanesulfinyl ketimines, reacted with nitroalkenes via stereoselective conjugate addition to give Michael adducts with opposite stereochemistry to that obtained using α-branched sulfinylketimines. In the presence of excess base (2.5 equiv t -BuOK), the adducts derived from α-linear ketimines were further stereoselectively deprotonated to afford the corresponding kinetically favorable N -sulfinyl (Z)-enamine derivatives in good yields with good stereoselectivities. A reaction model was proposed to rationalize the observed stereochemistry. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00397881
- Volume :
- 54
- Issue :
- 19
- Database :
- Academic Search Index
- Journal :
- Synthesis
- Publication Type :
- Academic Journal
- Accession number :
- 159194808
- Full Text :
- https://doi.org/10.1055/s-0040-1719925