Notable structural property of 2,4,6-Tri- tert -butylanilide enolates: Interconversion between the rotamers and their reactivity

Yusuke Ohnishi; Masahi Sakai; Shouta Nakao; Osamu Kitagawa

doi:10.1021/ol200814m

Notable structural property of 2,4,6-Tri- tert -butylanilide enolates: Interconversion between the rotamers and their reactivity

Yusuke Ohnishi, Masahi Sakai, Shouta Nakao, Osamu Kitagawa

研究成果: Article › 査読

9 被引用数 (Scopus)

抄録

Interconversion between the separable 2,4,6-tri-tert-butylanilide rotamers was found to easily occur through formation of the lithium enolate. Protonation of the anilide enolate gave the anilide rotamer mixture of E-major. On the other hand, reactions of lithium enolate prepared from 2,4,6-tri-tert- butylpropionanilide with alkyl bromides preferentially afforded a Z-rotamer of alkylated products.

本文言語	English
ページ（範囲）	2840-2843
ページ数	4
ジャーナル	Organic Letters
巻	13
号	11
DOI	https://doi.org/10.1021/ol200814m
出版ステータス	Published - 2011 6月 3

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

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10.1021/ol200814m

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引用スタイル

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AU - Nakao, Shouta

AU - Kitagawa, Osamu

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N2 - Interconversion between the separable 2,4,6-tri-tert-butylanilide rotamers was found to easily occur through formation of the lithium enolate. Protonation of the anilide enolate gave the anilide rotamer mixture of E-major. On the other hand, reactions of lithium enolate prepared from 2,4,6-tri-tert- butylpropionanilide with alkyl bromides preferentially afforded a Z-rotamer of alkylated products.

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