An Intramolecular Heck reaction that Prefers a 5-endo- to a 6-exo-trig Cyclization Pathway

Paulo Vital; Per-Ola Norrby; David Ackland Tanner

doi:10.1055/s-2006-951504

An Intramolecular Heck reaction that Prefers a 5-endo- to a 6-exo-trig Cyclization Pathway

Paulo Vital
, Per-Ola Norrby
, David Ackland Tanner

Department of Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

A regioselective aromatic Claisen rearrangement was used to prepare 17a, the precursor of triflate 17e. The intramolecular Heck reaction of 17e is promoted only by bidentate phosphine ligands, giving exclusively and in excellent yield 20, the product of a 5-endo-trig cyclization, despite the possibility for a 6-exo-trig pathway.

Original language	English
Journal	SYNLETT: Accounts and Rapid Communications in Chemical Synthesis
Issue number	18
Pages (from-to)	3140-3144
ISSN	0936-5214
DOIs	https://doi.org/10.1055/s-2006-951504
Publication status	Published - 2006

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title = "An Intramolecular Heck reaction that Prefers a 5-endo- to a 6-exo-trig Cyclization Pathway",

abstract = "A regioselective aromatic Claisen rearrangement was used to prepare 17a, the precursor of triflate 17e. The intramolecular Heck reaction of 17e is promoted only by bidentate phosphine ligands, giving exclusively and in excellent yield 20, the product of a 5-endo-trig cyclization, despite the possibility for a 6-exo-trig pathway. ",

author = "Paulo Vital and Per-Ola Norrby and Tanner, \{David Ackland\}",

year = "2006",

doi = "10.1055/s-2006-951504",

language = "English",

pages = "3140--3144",

journal = "SYNLETT: Accounts and Rapid Communications in Chemical Synthesis",

issn = "0936-5214",

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TY - JOUR

T1 - An Intramolecular Heck reaction that Prefers a 5-endo- to a 6-exo-trig Cyclization Pathway

AU - Vital, Paulo

AU - Norrby, Per-Ola

AU - Tanner, David Ackland

PY - 2006

Y1 - 2006

N2 - A regioselective aromatic Claisen rearrangement was used to prepare 17a, the precursor of triflate 17e. The intramolecular Heck reaction of 17e is promoted only by bidentate phosphine ligands, giving exclusively and in excellent yield 20, the product of a 5-endo-trig cyclization, despite the possibility for a 6-exo-trig pathway.

AB - A regioselective aromatic Claisen rearrangement was used to prepare 17a, the precursor of triflate 17e. The intramolecular Heck reaction of 17e is promoted only by bidentate phosphine ligands, giving exclusively and in excellent yield 20, the product of a 5-endo-trig cyclization, despite the possibility for a 6-exo-trig pathway.

U2 - 10.1055/s-2006-951504

DO - 10.1055/s-2006-951504

M3 - Journal article

SN - 0936-5214

SP - 3140

EP - 3144

JO - SYNLETT: Accounts and Rapid Communications in Chemical Synthesis

JF - SYNLETT: Accounts and Rapid Communications in Chemical Synthesis

IS - 18

ER -

An Intramolecular Heck reaction that Prefers a 5-endo- to a 6-exo-trig Cyclization Pathway

Abstract

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