Stereospecific formation of tetrasubstituted centres from trisubstituted centres during dearomatising anionic cyclisations

Ryan A. Bragg; Jonathan Clayden

doi:10.1016/S0040-4039(99)01765-7

Stereospecific formation of tetrasubstituted centres from trisubstituted centres during dearomatising anionic cyclisations

Ryan A. Bragg, Jonathan Clayden^*

^*Corresponding author for this work

School of Chemistry

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

36 Citations (Scopus)

Abstract

Dearomatising anionic cyclisation of tertiary naphthamides bearing chiral N-substituents (such as α-methylbenzyl) proceeds with overall retention of configuration at the newly formed tetrasubstituted chiral centre. The cyclisation is stereospecific overall, with the configuration of the starting trisubstituted stereogenic centre controlling the stereochemistry of the product. Highly substituted pyrrolidinone rings may be formed as single enantiomers from enantiomerically pure starting materials.

Original language	English
Pages (from-to)	8323-8326
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	48
DOIs	https://doi.org/10.1016/S0040-4039(99)01765-7
Publication status	Published - 26 Nov 1999

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Organic & Biological

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title = "Stereospecific formation of tetrasubstituted centres from trisubstituted centres during dearomatising anionic cyclisations",

abstract = "Dearomatising anionic cyclisation of tertiary naphthamides bearing chiral N-substituents (such as α-methylbenzyl) proceeds with overall retention of configuration at the newly formed tetrasubstituted chiral centre. The cyclisation is stereospecific overall, with the configuration of the starting trisubstituted stereogenic centre controlling the stereochemistry of the product. Highly substituted pyrrolidinone rings may be formed as single enantiomers from enantiomerically pure starting materials.",

author = "Bragg, \{Ryan A.\} and Jonathan Clayden",

year = "1999",

month = nov,

day = "26",

doi = "10.1016/S0040-4039(99)01765-7",

language = "English",

volume = "40",

pages = "8323--8326",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - Stereospecific formation of tetrasubstituted centres from trisubstituted centres during dearomatising anionic cyclisations

AU - Bragg, Ryan A.

AU - Clayden, Jonathan

PY - 1999/11/26

Y1 - 1999/11/26

N2 - Dearomatising anionic cyclisation of tertiary naphthamides bearing chiral N-substituents (such as α-methylbenzyl) proceeds with overall retention of configuration at the newly formed tetrasubstituted chiral centre. The cyclisation is stereospecific overall, with the configuration of the starting trisubstituted stereogenic centre controlling the stereochemistry of the product. Highly substituted pyrrolidinone rings may be formed as single enantiomers from enantiomerically pure starting materials.

AB - Dearomatising anionic cyclisation of tertiary naphthamides bearing chiral N-substituents (such as α-methylbenzyl) proceeds with overall retention of configuration at the newly formed tetrasubstituted chiral centre. The cyclisation is stereospecific overall, with the configuration of the starting trisubstituted stereogenic centre controlling the stereochemistry of the product. Highly substituted pyrrolidinone rings may be formed as single enantiomers from enantiomerically pure starting materials.

UR - https://www.scopus.com/pages/publications/0033607425

U2 - 10.1016/S0040-4039(99)01765-7

DO - 10.1016/S0040-4039(99)01765-7

M3 - Article (Academic Journal)

AN - SCOPUS:0033607425

SN - 0040-4039

VL - 40

SP - 8323

EP - 8326

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 48

ER -

Stereospecific formation of tetrasubstituted centres from trisubstituted centres during dearomatising anionic cyclisations

Abstract

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