Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 13, Issue 8, Pages 2330-2340Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob02329c
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Funding
- EPSRC
- National Project FIRB - Futuro in Ricerca - Italian MIUR [CINECA RBFR083M5N]
- Laboratorio SISTEMA - Italian MIUR [PONa300369]
- Regional project Reti di Laboratori Pubblici di Ricerca [20]
- Engineering and Physical Sciences Research Council [EP/K039547/1] Funding Source: researchfish
- EPSRC [EP/K039547/1] Funding Source: UKRI
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The addition of n-butyllithium to alkenylthiocarbamates in the presence of (-)-sparteine or the (+)-sparteine surrogate leads to asymmetric carbolithiation, and returns enantiomerically enriched thiocarbamate derivatives of secondary thiols. In THF, with the (+)-sparteine surrogate, in situ aryl migration leads to an enantiomerically enriched tertiary thiol derivative. Remarkably, the two pseudoenantiomeric chiral ligands do not always give enantiomeric products, probably as a result of a complex interplay of kinetic and thermodynamic control. In situ IR and NMR studies of a stable, hindered lithiated thiocarbamate demonstrated its chemical and configurational stability over a period of hours at 0 degrees C.
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