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

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	2840-2843
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	11
DOIs	https://doi.org/10.1021/ol200814m
Publication status	Published - 2011 Jun 3

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol200814m

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abstract = "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.",

author = "Yusuke Ohnishi and Masahi Sakai and Shouta Nakao and Osamu Kitagawa",

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T1 - Notable structural property of 2,4,6-Tri- tert -butylanilide enolates

T2 - Interconversion between the rotamers and their reactivity

AU - Ohnishi, Yusuke

AU - Sakai, Masahi

AU - Nakao, Shouta

AU - Kitagawa, Osamu

PY - 2011/6/3

Y1 - 2011/6/3

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.

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

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