Chemistry Letters p. 759 - 760 (1999)
Update date:2022-08-17
Topics:
Tomooka, Katsuhiko
Shimizu, Hideo
Inoue, Tadashi
Shibata, Hikaru
Nakai, Takeshi
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.
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