1,2-carbamoyl migration on enantio-enriched α-lithioalkyl carbamates generated with s-butyllithium/sparteine: Steric course and mechanism

Katsuhiko Tomooka, Hideo Shimizu, Tadashi Inoue, Hikaru Shibata, Takeshi Nakai

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)759-760
Number of pages2
JournalChemistry Letters
Issue number8
DOIs
Publication statusPublished - Jan 1 1999

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Bearings (structural)
Sparteine
Carbamates
Amides
Ether
Temperature
butyllithium

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

1,2-carbamoyl migration on enantio-enriched α-lithioalkyl carbamates generated with s-butyllithium/sparteine : Steric course and mechanism. / Tomooka, Katsuhiko; Shimizu, Hideo; Inoue, Tadashi; Shibata, Hikaru; Nakai, Takeshi.

In: Chemistry Letters, No. 8, 01.01.1999, p. 759-760.

Research output: Contribution to journalArticle

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