BF3·Et2O and trifluoroacetic acid/triethyl amine-mediated synthesis of functionalized piperidines

Amar R. Mohite; Prakash R. Sultane; Ramakrishna G. Bhat

doi:10.1016/j.tetlet.2011.10.072

BF₃·Et₂O and trifluoroacetic acid/triethyl amine-mediated synthesis of functionalized piperidines

Amar R. Mohite, Prakash R. Sultane, Ramakrishna G. Bhat

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

16 Scopus citations

Abstract

A two-step short and efficient strategy for the synthesis of substituted piperidones and piperidines in high diastereoselectivity (only trans-configuration), by employing cascade type reaction using BF ₃·Et₂O or by carrying out one pot deprotection of ^tBoc group followed by intramolecular aza-Michael addition of α,β-unsaturated beta keto esters has been developed. Using a similar strategy a short access to hydroxy pipecolic acid is also described. Very simple and rapid experimental procedures involving mild conditions and only one or two chromatographic purifications are the main features of the process.

Original language	English
Pages (from-to)	30-35
Number of pages	6
Journal	Tetrahedron Letters
Volume	53
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2011.10.072
State	Published - 4 Jan 2012
Externally published	Yes

Keywords

Cyclization
Knoevenagel condensation
Michael addition
Nitrogen heterocycles
Piperidines

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2011.10.072

Cite this

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title = "BF3·Et2O and trifluoroacetic acid/triethyl amine-mediated synthesis of functionalized piperidines",

abstract = "A two-step short and efficient strategy for the synthesis of substituted piperidones and piperidines in high diastereoselectivity (only trans-configuration), by employing cascade type reaction using BF 3·Et2O or by carrying out one pot deprotection of tBoc group followed by intramolecular aza-Michael addition of α,β-unsaturated beta keto esters has been developed. Using a similar strategy a short access to hydroxy pipecolic acid is also described. Very simple and rapid experimental procedures involving mild conditions and only one or two chromatographic purifications are the main features of the process.",

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AU - Mohite, Amar R.

AU - Sultane, Prakash R.

AU - Bhat, Ramakrishna G.

N1 - Funding Information: A.R.M. and authors thank the IISER-Pune and the CSIR, New Delhi, India for the generous financial support.

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AB - A two-step short and efficient strategy for the synthesis of substituted piperidones and piperidines in high diastereoselectivity (only trans-configuration), by employing cascade type reaction using BF 3·Et2O or by carrying out one pot deprotection of tBoc group followed by intramolecular aza-Michael addition of α,β-unsaturated beta keto esters has been developed. Using a similar strategy a short access to hydroxy pipecolic acid is also described. Very simple and rapid experimental procedures involving mild conditions and only one or two chromatographic purifications are the main features of the process.

KW - Cyclization

KW - Knoevenagel condensation

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KW - Nitrogen heterocycles

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