2,2- and 2,6-diarylpiperidines by aryl migration within lithiated urea derivatives of tetrahydropyridines

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2,2- and 2,6-diarylpiperidines by aryl migration within lithiated urea derivatives of tetrahydropyridines. / Tait, Michael B.; Butterworth, Sam; Clayden, Jonathan.

In: Organic Letters, Vol. 17, No. 5, 06.03.2015, p. 1236-1239.

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@article{6dc1893fdbc94326be8c3e8f81198ad9,
title = "2,2- and 2,6-diarylpiperidines by aryl migration within lithiated urea derivatives of tetrahydropyridines",
abstract = "2-Aryltetrahydropyridines formed by anionic cyclization or ring-closing metathesis were converted to their N′-aryl urea derivatives. Depending on the position of the unsaturation within the tetrahydropyridine ring, metalation by deprotonative lithiation or carbolithiation led to migration of the N′-aryl substituent to the 2- or 6-position via intramolecular nucleophilic attack of a benzylic organolithium on the aryl ring. The products are a range of 2,2-, 2,2,3-, and 2,6-polysubstituted piperidine derivatives. Related chemistry was observed in pyrroline homologues.",
author = "Tait, {Michael B.} and Sam Butterworth and Jonathan Clayden",
year = "2015",
month = mar,
day = "6",
doi = "10.1021/acs.orglett.5b00199",
language = "English",
volume = "17",
pages = "1236--1239",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "5",

}

RIS

TY - JOUR

T1 - 2,2- and 2,6-diarylpiperidines by aryl migration within lithiated urea derivatives of tetrahydropyridines

AU - Tait, Michael B.

AU - Butterworth, Sam

AU - Clayden, Jonathan

PY - 2015/3/6

Y1 - 2015/3/6

N2 - 2-Aryltetrahydropyridines formed by anionic cyclization or ring-closing metathesis were converted to their N′-aryl urea derivatives. Depending on the position of the unsaturation within the tetrahydropyridine ring, metalation by deprotonative lithiation or carbolithiation led to migration of the N′-aryl substituent to the 2- or 6-position via intramolecular nucleophilic attack of a benzylic organolithium on the aryl ring. The products are a range of 2,2-, 2,2,3-, and 2,6-polysubstituted piperidine derivatives. Related chemistry was observed in pyrroline homologues.

AB - 2-Aryltetrahydropyridines formed by anionic cyclization or ring-closing metathesis were converted to their N′-aryl urea derivatives. Depending on the position of the unsaturation within the tetrahydropyridine ring, metalation by deprotonative lithiation or carbolithiation led to migration of the N′-aryl substituent to the 2- or 6-position via intramolecular nucleophilic attack of a benzylic organolithium on the aryl ring. The products are a range of 2,2-, 2,2,3-, and 2,6-polysubstituted piperidine derivatives. Related chemistry was observed in pyrroline homologues.

UR - http://www.scopus.com/inward/record.url?scp=84924255612&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.5b00199

DO - 10.1021/acs.orglett.5b00199

M3 - Article

C2 - 25692395

AN - SCOPUS:84924255612

VL - 17

SP - 1236

EP - 1239

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 5

ER -