An efficient synthesis of optically active axially chiral anilide and its application to iodine-mediated asymmetric Diels-Alder reaction

Osamu Kitagawa, Hirotaka Izawa, Takeo Taguchi, Motoo Shiro

Research output: Contribution to journalArticle

71 Citations (Scopus)

Abstract

A new axially chiral N-acryl-N-allyl-o-tert-butylanilide with high optical purity (96-97 %ee) was prepared in good yield from (S)-O-acetyl lactic acid and N-allyl o-t-butylaniline. Iodine mediated Diels-Alder reaction of the axially chiral N-acryl anilide with cyclopentadiene or isoprene proceeded with high diastereoselectivity.

Original languageEnglish
Pages (from-to)4447-4450
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number25
DOIs
Publication statusPublished - 1997 Jun 23
Externally publishedYes

Fingerprint

Anilides
Cyclopentanes
Iodine
Lactic Acid
isoprene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

An efficient synthesis of optically active axially chiral anilide and its application to iodine-mediated asymmetric Diels-Alder reaction. / Kitagawa, Osamu; Izawa, Hirotaka; Taguchi, Takeo; Shiro, Motoo.

In: Tetrahedron Letters, Vol. 38, No. 25, 23.06.1997, p. 4447-4450.

Research output: Contribution to journalArticle

@article{9f22905c9b314d4584e7fb2bda66cb75,
title = "An efficient synthesis of optically active axially chiral anilide and its application to iodine-mediated asymmetric Diels-Alder reaction",
abstract = "A new axially chiral N-acryl-N-allyl-o-tert-butylanilide with high optical purity (96-97 {\%}ee) was prepared in good yield from (S)-O-acetyl lactic acid and N-allyl o-t-butylaniline. Iodine mediated Diels-Alder reaction of the axially chiral N-acryl anilide with cyclopentadiene or isoprene proceeded with high diastereoselectivity.",
author = "Osamu Kitagawa and Hirotaka Izawa and Takeo Taguchi and Motoo Shiro",
year = "1997",
month = "6",
day = "23",
doi = "10.1016/S0040-4039(97)00928-3",
language = "English",
volume = "38",
pages = "4447--4450",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "25",

}

TY - JOUR

T1 - An efficient synthesis of optically active axially chiral anilide and its application to iodine-mediated asymmetric Diels-Alder reaction

AU - Kitagawa, Osamu

AU - Izawa, Hirotaka

AU - Taguchi, Takeo

AU - Shiro, Motoo

PY - 1997/6/23

Y1 - 1997/6/23

N2 - A new axially chiral N-acryl-N-allyl-o-tert-butylanilide with high optical purity (96-97 %ee) was prepared in good yield from (S)-O-acetyl lactic acid and N-allyl o-t-butylaniline. Iodine mediated Diels-Alder reaction of the axially chiral N-acryl anilide with cyclopentadiene or isoprene proceeded with high diastereoselectivity.

AB - A new axially chiral N-acryl-N-allyl-o-tert-butylanilide with high optical purity (96-97 %ee) was prepared in good yield from (S)-O-acetyl lactic acid and N-allyl o-t-butylaniline. Iodine mediated Diels-Alder reaction of the axially chiral N-acryl anilide with cyclopentadiene or isoprene proceeded with high diastereoselectivity.

UR - http://www.scopus.com/inward/record.url?scp=0030950922&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0030950922&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(97)00928-3

DO - 10.1016/S0040-4039(97)00928-3

M3 - Article

AN - SCOPUS:0030950922

VL - 38

SP - 4447

EP - 4450

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 25

ER -