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