1,2-Carbamoyl Migration on Enantio-enriched <i>α</i>-Lithioalkyl Carbamates Generated with <i>s</i>-Butyllithium/Sparteine: Steric Course and Mechanism
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- Katsuhiko Tomooka
- Department of Chemical Technology, Tokyo Institute of TechnologyMeguro-ku, Tokyo
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- Hideo Shimizu
- Department of Chemical Technology, Tokyo Institute of TechnologyMeguro-ku, Tokyo
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- Tadashi Inoue
- Department of Chemical Technology, Tokyo Institute of TechnologyMeguro-ku, Tokyo
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- Hikaru Shibata
- Department of Chemical Technology, Tokyo Institute of TechnologyMeguro-ku, Tokyo
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- Takeshi Nakai
- Department of Chemical Technology, Tokyo Institute of TechnologyMeguro-ku, Tokyo
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<jats:title>Abstract</jats:title> <jats:p>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.</jats:p>
収録刊行物
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- Chemistry Letters
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Chemistry Letters 28 (8), 759-760, 1999-08-01
Oxford University Press (OUP)
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詳細情報
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- CRID
- 1360002219109710976
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- NII論文ID
- 10004703066
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- NII書誌ID
- AA00603318
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- ISSN
- 13480715
- 03667022
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