Highly enantioselective organocatalytic synthesis of piperidines. Formal synthesis of (-)-Paroxetine

Guillem Valero; Jiri Schimer; Ivana Cisarova; Jan Vesely; Albert Moyano; Ramon Rios

doi:10.1016/j.tetlet.2009.02.049

Highly enantioselective organocatalytic synthesis of piperidines. Formal synthesis of (-)-Paroxetine

Guillem Valero
, Jiri Schimer
, Ivana Cisarova
, Jan Vesely
, Albert Moyano
, Ramon Rios

Chemistry

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

95 Scopus citations

Abstract

A highly enantioselective organocatalytic synthesis of piperidines is reported. The reaction is catalyzed by simple and commercially available secondary amines, affording the corresponding adducts with high yields and enantioselectivities. Moreover, this reaction is used for the formal synthesis of (-)-Paroxetine, a blockbuster drug, in only three steps.

Original language	British English
Pages (from-to)	1943-1946
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	17
DOIs	https://doi.org/10.1016/j.tetlet.2009.02.049
State	Published - 29 Apr 2009

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title = "Highly enantioselective organocatalytic synthesis of piperidines. Formal synthesis of (-)-Paroxetine",

abstract = "A highly enantioselective organocatalytic synthesis of piperidines is reported. The reaction is catalyzed by simple and commercially available secondary amines, affording the corresponding adducts with high yields and enantioselectivities. Moreover, this reaction is used for the formal synthesis of (-)-Paroxetine, a blockbuster drug, in only three steps.",

author = "Guillem Valero and Jiri Schimer and Ivana Cisarova and Jan Vesely and Albert Moyano and Ramon Rios",

note = "Funding Information: We would like to thank J. Terr{\'o}n, M. V{\'a}zquez, and M. Spiropulu for useful comments and experimental information. This work has been partially supported by the DGICYT (Spain) under Projects No. FPA2000-0956 and No. BFM2002-01003. ",

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T1 - Highly enantioselective organocatalytic synthesis of piperidines. Formal synthesis of (-)-Paroxetine

AU - Valero, Guillem

AU - Schimer, Jiri

AU - Cisarova, Ivana

AU - Vesely, Jan

AU - Moyano, Albert

AU - Rios, Ramon

N1 - Funding Information: We would like to thank J. Terrón, M. Vázquez, and M. Spiropulu for useful comments and experimental information. This work has been partially supported by the DGICYT (Spain) under Projects No. FPA2000-0956 and No. BFM2002-01003.

PY - 2009/4/29

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N2 - A highly enantioselective organocatalytic synthesis of piperidines is reported. The reaction is catalyzed by simple and commercially available secondary amines, affording the corresponding adducts with high yields and enantioselectivities. Moreover, this reaction is used for the formal synthesis of (-)-Paroxetine, a blockbuster drug, in only three steps.

AB - A highly enantioselective organocatalytic synthesis of piperidines is reported. The reaction is catalyzed by simple and commercially available secondary amines, affording the corresponding adducts with high yields and enantioselectivities. Moreover, this reaction is used for the formal synthesis of (-)-Paroxetine, a blockbuster drug, in only three steps.

UR - https://www.scopus.com/pages/publications/61749096057

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DO - 10.1016/j.tetlet.2009.02.049

M3 - Article

AN - SCOPUS:61749096057

SN - 0040-4039

VL - 50

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EP - 1946

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -

Highly enantioselective organocatalytic synthesis of piperidines. Formal synthesis of (-)-Paroxetine

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