Erratum: A new synthesis of spiropyrrolidine-tetralones via an unexpected formal ring-contraction of 4-disubstituted piperidine to 3-disubstituted pyrrolidine (Tetrahedron Letters (2010) 51 (6415-6417))

Full text of DOI:10.1016/j.tetlet.2010.11.047

Tetrahedron Letters 52 (2011) 469
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Tetrahedron Letters
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Corrigendum
Corrigendum to ‘‘A new synthesis of spiropyrrolidine-tetralones via
an unexpected formal ring-contraction of 4-disubstituted piperidine to
3-disubstituted pyrrolidine’’ [Tetrahedron Lett. 51 (2010) 6415–6417]
⇑
Upul K. Bandarage , Robert J. Davies
Department of Medicinal Chemistry, Vertex Pharmaceutical Inc., 130 Waverly Street, Cambridge, MA 02139, USA
The authors regret that when this manuscript was published
Ref. 8 was not cited in the correct sentence. The updated text
and relevant reference are as follows:
When the piperidine nitrogen was deactivated with a boc group
in substrates similar to 6, no ring contraction was observed.
Instead, the desired piperidine nitrile was isolated in high yield.8
The opening of bridged bicyclic quaternary salts with nucleophiles
is unusual and there are relatively few examples of ring contrac-
tions via bicyclic salts in the literature.
Reference
Boc
N
Boc
N
F
F
1. MsCl, Et3N, DCM
8.
2. NaCN, DMSO
100 oC, 18 hr
78%
OH
CN
DOI of original article: 10.1016/j.tetlet.2010.09.142
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Corresponding author. Tel.: +1 617 444 6882; fax: +1 617 444 7827.
E-mail address: upul_bandarage@vrtx.com (U.K. Bandarage).
0040-4039/$ - see front matter Ó 2010 Elsevier Ltd. All rights reserved.
doi:10.1016/j.tetlet.2010.11.047