Alkyl N,N-diisopropylcarbamates, when lithiated with s-BuLi/(−)-sparteine in ether at −78 °C followed by warming to room temperature, are shown to undergo the 1,2-carbamoyl migration to give the α-hydroxy amides in >95% ee with complete retention of configuration at the Li-bearing carbanion terminus. An addition-elimination mechanism is proposed.
No takes yet. Share an insight, caveat, or question.
Tomooka et al. (1999) studied this question.
Synapse has enriched 4 closely related papers on similar clinical questions. Consider them for comparative context: