Catalytic iron-mediated ene carbocyclizations of trienes

The stereoselecitve preparation of N-acylpiperidines

Beckie E. Takacs, James M Takacs

Research output: Contribution to journalArticle

37 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)2865-2868
Number of pages4
JournalTetrahedron Letters
Volume31
Issue number20
DOIs
StatePublished - Jan 1 1990

Fingerprint

Alkenes
Isomers
Nitrogen
Iron
Derivatives
Atoms
Substrates

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Catalytic iron-mediated ene carbocyclizations of trienes : The stereoselecitve preparation of N-acylpiperidines. / E. Takacs, Beckie; Takacs, James M.

In: Tetrahedron Letters, Vol. 31, No. 20, 01.01.1990, p. 2865-2868.

Research output: Contribution to journalArticle

@article{b4cc97f33fbe4257b4f071eed9447103,
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 Takacs, {James M}",
year = "1990",
month = "1",
day = "1",
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",
number = "20",

}

TY - JOUR

T1 - Catalytic iron-mediated ene carbocyclizations of trienes

T2 - The stereoselecitve preparation of N-acylpiperidines

AU - E. Takacs, Beckie

AU - Takacs, James M

PY - 1990/1/1

Y1 - 1990/1/1

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.

UR - http://www.scopus.com/inward/record.url?scp=0025300503&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0025300503&partnerID=8YFLogxK

U2 - 10.1016/0040-4039(90)80168-L

DO - 10.1016/0040-4039(90)80168-L

M3 - Article

VL - 31

SP - 2865

EP - 2868

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 20

ER -