Diels-Alder reaction of N-allylic enamides and lactam derivatives through iodine mediated activation

Osamu Kitagawa, Katsuyuki Aoki, Tadashi Inoue, Takeo Taguchi

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

The Diels-Alder reaction of N-allylic enamide and α,β-unsaturated lactam derivatives proceeded in the presence of I2 at low temperature through a cationic iodolactonization intermediate. With some substrates, this method of activation was proved to be more effective than by use of Lewis acids.

Original languageEnglish
Pages (from-to)593-596
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number4
DOIs
Publication statusPublished - 1995 Jan 23
Externally publishedYes

Fingerprint

Lactams
Lewis Acids
Iodine
Chemical activation
Derivatives
Substrates
Temperature

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Diels-Alder reaction of N-allylic enamides and lactam derivatives through iodine mediated activation. / Kitagawa, Osamu; Aoki, Katsuyuki; Inoue, Tadashi; Taguchi, Takeo.

In: Tetrahedron Letters, Vol. 36, No. 4, 23.01.1995, p. 593-596.

Research output: Contribution to journalArticle

Kitagawa, Osamu ; Aoki, Katsuyuki ; Inoue, Tadashi ; Taguchi, Takeo. / Diels-Alder reaction of N-allylic enamides and lactam derivatives through iodine mediated activation. In: Tetrahedron Letters. 1995 ; Vol. 36, No. 4. pp. 593-596.
@article{1f5cbff19e1a4b869935fee32cfa104f,
title = "Diels-Alder reaction of N-allylic enamides and lactam derivatives through iodine mediated activation",
abstract = "The Diels-Alder reaction of N-allylic enamide and α,β-unsaturated lactam derivatives proceeded in the presence of I2 at low temperature through a cationic iodolactonization intermediate. With some substrates, this method of activation was proved to be more effective than by use of Lewis acids.",
author = "Osamu Kitagawa and Katsuyuki Aoki and Tadashi Inoue and Takeo Taguchi",
year = "1995",
month = "1",
day = "23",
doi = "10.1016/0040-4039(94)02261-9",
language = "English",
volume = "36",
pages = "593--596",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "4",

}

TY - JOUR

T1 - Diels-Alder reaction of N-allylic enamides and lactam derivatives through iodine mediated activation

AU - Kitagawa, Osamu

AU - Aoki, Katsuyuki

AU - Inoue, Tadashi

AU - Taguchi, Takeo

PY - 1995/1/23

Y1 - 1995/1/23

N2 - The Diels-Alder reaction of N-allylic enamide and α,β-unsaturated lactam derivatives proceeded in the presence of I2 at low temperature through a cationic iodolactonization intermediate. With some substrates, this method of activation was proved to be more effective than by use of Lewis acids.

AB - The Diels-Alder reaction of N-allylic enamide and α,β-unsaturated lactam derivatives proceeded in the presence of I2 at low temperature through a cationic iodolactonization intermediate. With some substrates, this method of activation was proved to be more effective than by use of Lewis acids.

UR - http://www.scopus.com/inward/record.url?scp=0028839003&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0028839003&partnerID=8YFLogxK

U2 - 10.1016/0040-4039(94)02261-9

DO - 10.1016/0040-4039(94)02261-9

M3 - Article

VL - 36

SP - 593

EP - 596

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 4

ER -