Catalytic iron-mediated ene carbocyclizations of trienes: The stereoselecitve preparation of N-acylpiperidines

Beckie E. Takacs; James M. Takacs

doi:10.1016/0040-4039(90)80168-L

Catalytic iron-mediated ene carbocyclizations of trienes: The stereoselecitve preparation of N-acylpiperidines

Beckie E. Takacs, James M. Takacs

Chemistry

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

39 Scopus citations

Abstract

5- and 6-Aza-(2Z,8E)-2,8,10-undecatriene and a 6-aza-(3Z,9E)-3,9,11-dodecatriene derivatives, substrates containing a nitrogen atom in the chain connecting the 1,3-diene and alkene functionalities, undergo efficient, stereoselective [4+4]-ene carbocyclization to yield trans-disubstituted N-acylpiperidines. In contrast, the corresponding (2Z,8Z)-diastereonmer yields predominantly the corresponding cis isomer.

Original language	English (US)
Pages (from-to)	2865-2868
Number of pages	4
Journal	Tetrahedron Letters
Volume	31
Issue number	20
DOIs	https://doi.org/10.1016/0040-4039(90)80168-L
State	Published - 1990

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Catalytic iron-mediated ene carbocyclizations of trienes: The stereoselecitve preparation of N-acylpiperidines",

abstract = "5- and 6-Aza-(2Z,8E)-2,8,10-undecatriene and a 6-aza-(3Z,9E)-3,9,11-dodecatriene derivatives, substrates containing a nitrogen atom in the chain connecting the 1,3-diene and alkene functionalities, undergo efficient, stereoselective [4+4]-ene carbocyclization to yield trans-disubstituted N-acylpiperidines. In contrast, the corresponding (2Z,8Z)-diastereonmer yields predominantly the corresponding cis isomer.",

author = "{E. Takacs}, Beckie and {M. Takacs}, James",

year = "1990",

doi = "10.1016/0040-4039(90)80168-L",

language = "English (US)",

volume = "31",

pages = "2865--2868",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

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T1 - Catalytic iron-mediated ene carbocyclizations of trienes

T2 - The stereoselecitve preparation of N-acylpiperidines

AU - E. Takacs, Beckie

AU - M. Takacs, James

PY - 1990

Y1 - 1990

N2 - 5- and 6-Aza-(2Z,8E)-2,8,10-undecatriene and a 6-aza-(3Z,9E)-3,9,11-dodecatriene derivatives, substrates containing a nitrogen atom in the chain connecting the 1,3-diene and alkene functionalities, undergo efficient, stereoselective [4+4]-ene carbocyclization to yield trans-disubstituted N-acylpiperidines. In contrast, the corresponding (2Z,8Z)-diastereonmer yields predominantly the corresponding cis isomer.

AB - 5- and 6-Aza-(2Z,8E)-2,8,10-undecatriene and a 6-aza-(3Z,9E)-3,9,11-dodecatriene derivatives, substrates containing a nitrogen atom in the chain connecting the 1,3-diene and alkene functionalities, undergo efficient, stereoselective [4+4]-ene carbocyclization to yield trans-disubstituted N-acylpiperidines. In contrast, the corresponding (2Z,8Z)-diastereonmer yields predominantly the corresponding cis isomer.

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EP - 2868

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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