Variations in site of lithiation of N-[2-(4-methoxyphenyl)ethyl]pivalamide - Use in ring substitution

Keith Smith; Gamal A. El-Hiti; Mohammed B. Alshammari

doi:10.1055/s-0032-1317859

Variations in site of lithiation of N-[2-(4-methoxyphenyl)ethyl]pivalamide - Use in ring substitution

Keith Smith
, Gamal A. El-Hiti
, Mohammed B. Alshammari

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

6 Scopus citations

Abstract

Lithiation of N-[2-(4-methoxyphenyl)ethyl]pivalamide at -20 to 0 °C with three equivalents of n-BuLi in anhydrous THF, followed by reactions with various electrophiles, gives high yields of products involving ring substitution ortho to the pivaloylaminoethyl group, which was unexpected in view of earlier results reported with t-BuLi.

Original language	English
Pages (from-to)	117-119
Number of pages	3
Journal	Synlett
Volume	24
Issue number	1
DOIs	https://doi.org/10.1055/s-0032-1317859
State	Published - 2013
Externally published	Yes

Keywords

N -[2-(4-methoxyphenyl)ethyl]pivalamide
dilithium intermediate
directed lithiation
electrophile
synthesis

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10.1055/s-0032-1317859

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title = "Variations in site of lithiation of N-[2-(4-methoxyphenyl)ethyl]pivalamide - Use in ring substitution",

abstract = "Lithiation of N-[2-(4-methoxyphenyl)ethyl]pivalamide at -20 to 0 °C with three equivalents of n-BuLi in anhydrous THF, followed by reactions with various electrophiles, gives high yields of products involving ring substitution ortho to the pivaloylaminoethyl group, which was unexpected in view of earlier results reported with t-BuLi.",

keywords = "N -[2-(4-methoxyphenyl)ethyl]pivalamide, dilithium intermediate, directed lithiation, electrophile, synthesis",

author = "Keith Smith and El-Hiti, \{Gamal A.\} and Alshammari, \{Mohammed B.\}",

year = "2013",

doi = "10.1055/s-0032-1317859",

language = "English",

volume = "24",

pages = "117--119",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

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T1 - Variations in site of lithiation of N-[2-(4-methoxyphenyl)ethyl]pivalamide - Use in ring substitution

AU - Smith, Keith

AU - El-Hiti, Gamal A.

AU - Alshammari, Mohammed B.

PY - 2013

Y1 - 2013

N2 - Lithiation of N-[2-(4-methoxyphenyl)ethyl]pivalamide at -20 to 0 °C with three equivalents of n-BuLi in anhydrous THF, followed by reactions with various electrophiles, gives high yields of products involving ring substitution ortho to the pivaloylaminoethyl group, which was unexpected in view of earlier results reported with t-BuLi.

AB - Lithiation of N-[2-(4-methoxyphenyl)ethyl]pivalamide at -20 to 0 °C with three equivalents of n-BuLi in anhydrous THF, followed by reactions with various electrophiles, gives high yields of products involving ring substitution ortho to the pivaloylaminoethyl group, which was unexpected in view of earlier results reported with t-BuLi.

KW - N -[2-(4-methoxyphenyl)ethyl]pivalamide

KW - dilithium intermediate

KW - directed lithiation

KW - electrophile

KW - synthesis

UR - https://www.scopus.com/pages/publications/84871720715

U2 - 10.1055/s-0032-1317859

DO - 10.1055/s-0032-1317859

M3 - Article

AN - SCOPUS:84871720715

SN - 0936-5214

VL - 24

SP - 117

EP - 119

JO - Synlett

JF - Synlett

IS - 1

ER -

Variations in site of lithiation of N-[2-(4-methoxyphenyl)ethyl]pivalamide - Use in ring substitution

Abstract

Keywords

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