The use of the aza-Diels-Alder reaction in the synthesis of pinidine and other piperidine alkaloids

Patrick D. Bailey; Peter D. Smith; Keith M. Morgan; Georgina M. Rosair

doi:10.1016/S0040-4039(01)02149-9

The use of the aza-Diels-Alder reaction in the synthesis of pinidine and other piperidine alkaloids

Patrick D. Bailey, Peter D. Smith, Keith M. Morgan, Georgina M. Rosair

School of Engineering & Physical Sciences

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

17 Citations (Scopus)

Abstract

The imine Ph₂CHN=CHCO₂Et, generated from benzhydrylamine and ethyl glyoxylate, provides a Diels-Alder adduct with 1,3-pentadiene from which a range of cis-2,6-disubstituted piperidines can be accessed; the benzhydryl group confers high diastereocontrol for derivatising the six-membered ring, allowing access to 2,5,6-trisubstituted piperidines, and to 2,6-disubstituted piperidines such as pinidine. © 2002 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	1071-1074
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	6
DOIs	https://doi.org/10.1016/S0040-4039(01)02149-9
Publication status	Published - 4 Feb 2002

Keywords

Alkaloids
Diels-Alder reaction
Piperidines

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10.1016/S0040-4039(01)02149-9

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title = "The use of the aza-Diels-Alder reaction in the synthesis of pinidine and other piperidine alkaloids",

abstract = "The imine Ph2CHN=CHCO2Et, generated from benzhydrylamine and ethyl glyoxylate, provides a Diels-Alder adduct with 1,3-pentadiene from which a range of cis-2,6-disubstituted piperidines can be accessed; the benzhydryl group confers high diastereocontrol for derivatising the six-membered ring, allowing access to 2,5,6-trisubstituted piperidines, and to 2,6-disubstituted piperidines such as pinidine. {\textcopyright} 2002 Elsevier Science Ltd. All rights reserved.",

keywords = "Alkaloids, Diels-Alder reaction, Piperidines",

author = "Bailey, \{Patrick D.\} and Smith, \{Peter D.\} and Morgan, \{Keith M.\} and Rosair, \{Georgina M.\}",

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T1 - The use of the aza-Diels-Alder reaction in the synthesis of pinidine and other piperidine alkaloids

AU - Bailey, Patrick D.

AU - Smith, Peter D.

AU - Morgan, Keith M.

AU - Rosair, Georgina M.

PY - 2002/2/4

Y1 - 2002/2/4

N2 - The imine Ph2CHN=CHCO2Et, generated from benzhydrylamine and ethyl glyoxylate, provides a Diels-Alder adduct with 1,3-pentadiene from which a range of cis-2,6-disubstituted piperidines can be accessed; the benzhydryl group confers high diastereocontrol for derivatising the six-membered ring, allowing access to 2,5,6-trisubstituted piperidines, and to 2,6-disubstituted piperidines such as pinidine. © 2002 Elsevier Science Ltd. All rights reserved.

AB - The imine Ph2CHN=CHCO2Et, generated from benzhydrylamine and ethyl glyoxylate, provides a Diels-Alder adduct with 1,3-pentadiene from which a range of cis-2,6-disubstituted piperidines can be accessed; the benzhydryl group confers high diastereocontrol for derivatising the six-membered ring, allowing access to 2,5,6-trisubstituted piperidines, and to 2,6-disubstituted piperidines such as pinidine. © 2002 Elsevier Science Ltd. All rights reserved.

KW - Alkaloids

KW - Diels-Alder reaction

KW - Piperidines

UR - https://www.scopus.com/pages/publications/0037017027

U2 - 10.1016/S0040-4039(01)02149-9

DO - 10.1016/S0040-4039(01)02149-9

M3 - Article

SN - 0040-4039

VL - 43

SP - 1071

EP - 1074

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 6

ER -

The use of the aza-Diels-Alder reaction in the synthesis of pinidine and other piperidine alkaloids

Abstract

Keywords

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