Configurational stability and stereospecificity in the reactions of amide-stabilised organolithiums: A non-stereospecific tin-lithium exchange

Jonathan Clayden; Jennifer H. Pink

doi:10.1016/S0040-4039(97)00402-4

Configurational stability and stereospecificity in the reactions of amide-stabilised organolithiums: A non-stereospecific tin-lithium exchange

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

Diastereoisomers of laterally lithiated tertiary naphthamides are configurationally stable at the lithium-bearing stereogenic centre at -40°C. The syn diastereoisomer, which may be farmed by stereoselective deprotonation or stereospecific transmetallation, reacts stereospecifically, but both the tin-lithium exchange leading to the anti diastereoisomer and its subsequent reactions are characterised by an unprecedented lack of stereospecificity.

Original language	English
Pages (from-to)	2565-2568
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	14
DOIs	https://doi.org/10.1016/S0040-4039(97)00402-4
Publication status	Published - 7 Apr 1997

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title = "Configurational stability and stereospecificity in the reactions of amide-stabilised organolithiums: A non-stereospecific tin-lithium exchange",

abstract = "Diastereoisomers of laterally lithiated tertiary naphthamides are configurationally stable at the lithium-bearing stereogenic centre at -40°C. The syn diastereoisomer, which may be farmed by stereoselective deprotonation or stereospecific transmetallation, reacts stereospecifically, but both the tin-lithium exchange leading to the anti diastereoisomer and its subsequent reactions are characterised by an unprecedented lack of stereospecificity.",

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T1 - Configurational stability and stereospecificity in the reactions of amide-stabilised organolithiums

T2 - A non-stereospecific tin-lithium exchange

AU - Clayden, Jonathan

AU - Pink, Jennifer H.

PY - 1997/4/7

Y1 - 1997/4/7

N2 - Diastereoisomers of laterally lithiated tertiary naphthamides are configurationally stable at the lithium-bearing stereogenic centre at -40°C. The syn diastereoisomer, which may be farmed by stereoselective deprotonation or stereospecific transmetallation, reacts stereospecifically, but both the tin-lithium exchange leading to the anti diastereoisomer and its subsequent reactions are characterised by an unprecedented lack of stereospecificity.

AB - Diastereoisomers of laterally lithiated tertiary naphthamides are configurationally stable at the lithium-bearing stereogenic centre at -40°C. The syn diastereoisomer, which may be farmed by stereoselective deprotonation or stereospecific transmetallation, reacts stereospecifically, but both the tin-lithium exchange leading to the anti diastereoisomer and its subsequent reactions are characterised by an unprecedented lack of stereospecificity.

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U2 - 10.1016/S0040-4039(97)00402-4

DO - 10.1016/S0040-4039(97)00402-4

M3 - Article (Academic Journal)

AN - SCOPUS:0030942369

SN - 0040-4039

VL - 38

SP - 2565

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 14

ER -

Configurational stability and stereospecificity in the reactions of amide-stabilised organolithiums: A non-stereospecific tin-lithium exchange

Abstract

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