Bridgehead enolates: substitution and asymmetric desymmetrization of small bridged carbonyl compounds by lithium amide bases

GMP Giblin; DT Kirk; L Mitchell; Nigel Simpkins

doi:10.1021/ol034348l

Bridgehead enolates: substitution and asymmetric desymmetrization of small bridged carbonyl compounds by lithium amide bases

GMP Giblin, DT Kirk, L Mitchell, Nigel Simpkins

Chemistry

Research output: Contribution to journal › Article

24 Citations (Scopus)

Abstract

[reaction: see text] Contrary to expectations, a number of bridged carbonyl compounds undergo facile bridgehead metalation with lithium amide bases. Diketone, lactone, lactam, and imide functions are all demonstrated to participate in this type of "bridgehead enolate" chemistry, leading to a range of substituted products. Meso compounds can also be desymmetrized in very high ee by asymmetric bridgehead metalation.

Original language	English
Pages (from-to)	1673-1675
Number of pages	3
Journal	Organic Letters
Volume	5
Issue number	10
DOIs	https://doi.org/10.1021/ol034348l
Publication status	Published - 15 May 2003

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title = "Bridgehead enolates: substitution and asymmetric desymmetrization of small bridged carbonyl compounds by lithium amide bases",

abstract = "[reaction: see text] Contrary to expectations, a number of bridged carbonyl compounds undergo facile bridgehead metalation with lithium amide bases. Diketone, lactone, lactam, and imide functions are all demonstrated to participate in this type of {"}bridgehead enolate{"} chemistry, leading to a range of substituted products. Meso compounds can also be desymmetrized in very high ee by asymmetric bridgehead metalation.",

author = "GMP Giblin and DT Kirk and L Mitchell and Nigel Simpkins",

year = "2003",

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doi = "10.1021/ol034348l",

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T1 - Bridgehead enolates: substitution and asymmetric desymmetrization of small bridged carbonyl compounds by lithium amide bases

AU - Giblin, GMP

AU - Kirk, DT

AU - Mitchell, L

AU - Simpkins, Nigel

PY - 2003/5/15

Y1 - 2003/5/15

N2 - [reaction: see text] Contrary to expectations, a number of bridged carbonyl compounds undergo facile bridgehead metalation with lithium amide bases. Diketone, lactone, lactam, and imide functions are all demonstrated to participate in this type of "bridgehead enolate" chemistry, leading to a range of substituted products. Meso compounds can also be desymmetrized in very high ee by asymmetric bridgehead metalation.

AB - [reaction: see text] Contrary to expectations, a number of bridged carbonyl compounds undergo facile bridgehead metalation with lithium amide bases. Diketone, lactone, lactam, and imide functions are all demonstrated to participate in this type of "bridgehead enolate" chemistry, leading to a range of substituted products. Meso compounds can also be desymmetrized in very high ee by asymmetric bridgehead metalation.

U2 - 10.1021/ol034348l

DO - 10.1021/ol034348l

M3 - Article

C2 - 12735749

VL - 5

SP - 1673

EP - 1675

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Bridgehead enolates: substitution and asymmetric desymmetrization of small bridged carbonyl compounds by lithium amide bases

Abstract

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