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

doi:10.1246/cl.1999.759

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

研究成果: ジャーナルへの寄稿 › 学術誌 › 査読

27 被引用数 (Scopus)

抄録

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.

本文言語	英語
ページ（範囲）	759-760
ページ数	2
ジャーナル	Chemistry Letters
号	8
DOI	https://doi.org/10.1246/cl.1999.759
出版ステータス	出版済み - 1999
外部発表	はい

!!!All Science Journal Classification (ASJC) codes

化学 (全般)

文献へのアクセス

10.1246/cl.1999.759

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引用スタイル

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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.",

author = "Katsuhiko Tomooka and Hideo Shimizu and Tadashi Inoue and Hikaru Shibata and Takeshi Nakai",

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T2 - Steric course and mechanism

AU - Tomooka, Katsuhiko

AU - Shimizu, Hideo

AU - Inoue, Tadashi

AU - Shibata, Hikaru

AU - Nakai, Takeshi

PY - 1999

Y1 - 1999

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AB - 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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