Influencing the balance between ipso and ω nucleophile addition to (1-arylcyclohexadienyl)iron intermediates in alkaloid synthesis

G. Richard Stephenson; Christopher E. Anson; Andrei V. Malkov; Caroline Roe

doi:10.1002/ejoc.201200687

Influencing the balance between ipso and ω nucleophile addition to (1-arylcyclohexadienyl)iron intermediates in alkaloid synthesis

G. Richard Stephenson
, Christopher E. Anson
, Andrei V. Malkov
, Caroline Roe

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

9 Citations (Scopus)

Abstract

(1-Arylcyclohexadienyl)iron complexes are used in a synthesis of mesembrine and in an intramolecular spirocyclisation. Structural and spectroscopic data show that intermolecular ipso addition of nucleophiles is assisted by transfer of electron density from the arene to the metal complex, which occurs as the 1-aryldienyl structure flattens.

Original language	English
Pages (from-to)	4716-4732
Number of pages	17
Journal	European Journal of Organic Chemistry
Volume	2012
Issue number	25
DOIs	https://doi.org/10.1002/ejoc.201200687
Publication status	Published - 2012

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10.1002/ejoc.201200687

Cite this

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title = "Influencing the balance between ipso and ω nucleophile addition to (1-arylcyclohexadienyl)iron intermediates in alkaloid synthesis",

abstract = "(1-Arylcyclohexadienyl)iron complexes are used in a synthesis of mesembrine and in an intramolecular spirocyclisation. Structural and spectroscopic data show that intermolecular ipso addition of nucleophiles is assisted by transfer of electron density from the arene to the metal complex, which occurs as the 1-aryldienyl structure flattens.",

author = "Stephenson, \{G. Richard\} and Anson, \{Christopher E.\} and Malkov, \{Andrei V.\} and Caroline Roe",

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journal = "European Journal of Organic Chemistry",

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AU - Stephenson, G. Richard

AU - Anson, Christopher E.

AU - Malkov, Andrei V.

AU - Roe, Caroline

PY - 2012

Y1 - 2012

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AB - (1-Arylcyclohexadienyl)iron complexes are used in a synthesis of mesembrine and in an intramolecular spirocyclisation. Structural and spectroscopic data show that intermolecular ipso addition of nucleophiles is assisted by transfer of electron density from the arene to the metal complex, which occurs as the 1-aryldienyl structure flattens.

U2 - 10.1002/ejoc.201200687

DO - 10.1002/ejoc.201200687

M3 - Article

SN - 1099-0690

VL - 2012

SP - 4716

EP - 4732

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 25

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