Asymmetric synthesis of highly enantioenriched 2-substituted piperidines and 6-substituted piperidine-2-ones by a combination enantioselective hydrazone allylation with ring closing metathesis

Fengnu Piao; Mithilesh Kumar Mishra; Doo Ok Jang

doi:10.1016/j.tet.2012.06.061

Asymmetric synthesis of highly enantioenriched 2-substituted piperidines and 6-substituted piperidine-2-ones by a combination enantioselective hydrazone allylation with ring closing metathesis

Fengnu Piao, Mithilesh Kumar Mishra, Doo Ok Jang

Chemistry and Medical Chemistry

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

4 Citations (Scopus)

Abstract

An efficient method for the asymmetric synthesis of highly optically pure 2-substituted piperidines and 6-substituted piperidine-2-ones from aldehydes was developed by a sequence of enantioselective hydrazone allylation and ring closing metathesis. This method was found to be effective for a variety of substrates, showing substrate generality. The method's synthetic utility was illustrated in concise synthesis of the alkaloid (R)-(-)-coniine.

Original language	English
Pages (from-to)	7050-7055
Number of pages	6
Journal	Tetrahedron
Volume	68
Issue number	35
DOIs	https://doi.org/10.1016/j.tet.2012.06.061
Publication status	Published - 2012 Sept 2

Bibliographical note

Funding Information:
This work was supported by a Korea Research Foundation Grant ( KRF-2009-0074839 and KRF-2011-0021279), which was funded by the Korean Government.

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2012.06.061

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title = "Asymmetric synthesis of highly enantioenriched 2-substituted piperidines and 6-substituted piperidine-2-ones by a combination enantioselective hydrazone allylation with ring closing metathesis",

abstract = "An efficient method for the asymmetric synthesis of highly optically pure 2-substituted piperidines and 6-substituted piperidine-2-ones from aldehydes was developed by a sequence of enantioselective hydrazone allylation and ring closing metathesis. This method was found to be effective for a variety of substrates, showing substrate generality. The method's synthetic utility was illustrated in concise synthesis of the alkaloid (R)-(-)-coniine.",

author = "Fengnu Piao and Mishra, {Mithilesh Kumar} and Jang, {Doo Ok}",

note = "Funding Information: This work was supported by a Korea Research Foundation Grant ( KRF-2009-0074839 and KRF-2011-0021279), which was funded by the Korean Government. ",

year = "2012",

month = sep,

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doi = "10.1016/j.tet.2012.06.061",

language = "English",

volume = "68",

pages = "7050--7055",

journal = "Tetrahedron",

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Asymmetric synthesis of highly enantioenriched 2-substituted piperidines and 6-substituted piperidine-2-ones by a combination enantioselective hydrazone allylation with ring closing metathesis. / Piao, Fengnu; Mishra, Mithilesh Kumar; Jang, Doo Ok.

In: Tetrahedron, Vol. 68, No. 35, 02.09.2012, p. 7050-7055.

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

TY - JOUR

T1 - Asymmetric synthesis of highly enantioenriched 2-substituted piperidines and 6-substituted piperidine-2-ones by a combination enantioselective hydrazone allylation with ring closing metathesis

AU - Piao, Fengnu

AU - Mishra, Mithilesh Kumar

AU - Jang, Doo Ok

N1 - Funding Information: This work was supported by a Korea Research Foundation Grant ( KRF-2009-0074839 and KRF-2011-0021279), which was funded by the Korean Government.

PY - 2012/9/2

Y1 - 2012/9/2

N2 - An efficient method for the asymmetric synthesis of highly optically pure 2-substituted piperidines and 6-substituted piperidine-2-ones from aldehydes was developed by a sequence of enantioselective hydrazone allylation and ring closing metathesis. This method was found to be effective for a variety of substrates, showing substrate generality. The method's synthetic utility was illustrated in concise synthesis of the alkaloid (R)-(-)-coniine.

AB - An efficient method for the asymmetric synthesis of highly optically pure 2-substituted piperidines and 6-substituted piperidine-2-ones from aldehydes was developed by a sequence of enantioselective hydrazone allylation and ring closing metathesis. This method was found to be effective for a variety of substrates, showing substrate generality. The method's synthetic utility was illustrated in concise synthesis of the alkaloid (R)-(-)-coniine.

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JO - Tetrahedron

JF - Tetrahedron

IS - 35

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Asymmetric synthesis of highly enantioenriched 2-substituted piperidines and 6-substituted piperidine-2-ones by a combination enantioselective hydrazone allylation with ring closing metathesis

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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