Atroposelectivity in the reactions of laterally lithiated tertiary amides

Jonathan Clayden; Jennifer H. Pink

doi:10.1016/S0040-4039(97)00401-2

Atroposelectivity in the reactions of laterally lithiated tertiary amides

Jonathan Clayden^*, Jennifer H. Pink

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

44 Citations (Scopus)

Abstract

Lateral lithiation - electrophilic quench of 2-substituted N,N-dialkyl-1-naphthamides proceeds with high levels of diastereoselectivity in favour of one atropisomer of the product. Similar atroposelectivity may be observed in the reactions of 2-substituted benzamides, provided the products are trapped at low temperature by a subsequent in situ ortholithiation - alkylation reaction.

Original language	English
Pages (from-to)	2561-2564
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	14
DOIs	https://doi.org/10.1016/S0040-4039(97)00401-2
Publication status	Published - 7 Apr 1997

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title = "Atroposelectivity in the reactions of laterally lithiated tertiary amides",

abstract = "Lateral lithiation - electrophilic quench of 2-substituted N,N-dialkyl-1-naphthamides proceeds with high levels of diastereoselectivity in favour of one atropisomer of the product. Similar atroposelectivity may be observed in the reactions of 2-substituted benzamides, provided the products are trapped at low temperature by a subsequent in situ ortholithiation - alkylation reaction.",

author = "Jonathan Clayden and Pink, {Jennifer H.}",

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T1 - Atroposelectivity in the reactions of laterally lithiated tertiary amides

AU - Clayden, Jonathan

AU - Pink, Jennifer H.

PY - 1997/4/7

Y1 - 1997/4/7

N2 - Lateral lithiation - electrophilic quench of 2-substituted N,N-dialkyl-1-naphthamides proceeds with high levels of diastereoselectivity in favour of one atropisomer of the product. Similar atroposelectivity may be observed in the reactions of 2-substituted benzamides, provided the products are trapped at low temperature by a subsequent in situ ortholithiation - alkylation reaction.

AB - Lateral lithiation - electrophilic quench of 2-substituted N,N-dialkyl-1-naphthamides proceeds with high levels of diastereoselectivity in favour of one atropisomer of the product. Similar atroposelectivity may be observed in the reactions of 2-substituted benzamides, provided the products are trapped at low temperature by a subsequent in situ ortholithiation - alkylation reaction.

UR - http://www.scopus.com/inward/record.url?scp=0030971995&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(97)00401-2

DO - 10.1016/S0040-4039(97)00401-2

M3 - Article (Academic Journal)

AN - SCOPUS:0030971995

SN - 0040-4039

VL - 38

SP - 2561

EP - 2564

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 14

ER -

Atroposelectivity in the reactions of laterally lithiated tertiary amides

Abstract

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