Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction

Osamu Kitagawa, Masashi Takahashi, Masatoshi Yoshikawa, Takeo Taguchi

Research output: Contribution to journal › Article

80 Citations (Scopus)

Abstract

In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)2 catalyst, N-arylation of ortho-tert-butyl-NH-anilides with 4-nitroiodobenzene proceeds with high enantioselectivity (89-95% ee) to give optically active atropisomeric anilides possessing N-C chiral axis. Furthermore, the intramolecular version of the present catalytic asymmetric N-arylation gave atropisomeric lactams with high optical purity (94-96% ee).

Original languageEnglish
Pages (from-to)3676-3677
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number11
DOIs
Publication statusPublished - 2005 Mar 23
Externally publishedYes

Fingerprint

Anilides
Enantioselectivity
Lactams
Catalysts

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction. / Kitagawa, Osamu; Takahashi, Masashi; Yoshikawa, Masatoshi; Taguchi, Takeo.

In: Journal of the American Chemical Society, Vol. 127, No. 11, 23.03.2005, p. 3676-3677.

Research output: Contribution to journal › Article

Kitagawa, O, Takahashi, M, Yoshikawa, M & Taguchi, T 2005, 'Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction', Journal of the American Chemical Society, vol. 127, no. 11, pp. 3676-3677. https://doi.org/10.1021/ja042216x
Kitagawa O, Takahashi M, Yoshikawa M, Taguchi T. Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction. Journal of the American Chemical Society. 2005 Mar 23;127(11):3676-3677. https://doi.org/10.1021/ja042216x
Kitagawa, Osamu ; Takahashi, Masashi ; Yoshikawa, Masatoshi ; Taguchi, Takeo. / Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction. In: Journal of the American Chemical Society. 2005 ; Vol. 127, No. 11. pp. 3676-3677.
@article{35210dfc47e64cec9f1dae25a5083cbc,
title = "Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction",
abstract = "In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)2 catalyst, N-arylation of ortho-tert-butyl-NH-anilides with 4-nitroiodobenzene proceeds with high enantioselectivity (89-95{\%} ee) to give optically active atropisomeric anilides possessing N-C chiral axis. Furthermore, the intramolecular version of the present catalytic asymmetric N-arylation gave atropisomeric lactams with high optical purity (94-96{\%} ee).",
author = "Osamu Kitagawa and Masashi Takahashi and Masatoshi Yoshikawa and Takeo Taguchi",
year = "2005",
month = "3",
day = "23",
doi = "10.1021/ja042216x",
language = "English",
volume = "127",
pages = "3676--3677",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "11",

}

TY - JOUR

T1 - Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction

AU - Kitagawa, Osamu

AU - Takahashi, Masashi

AU - Yoshikawa, Masatoshi

AU - Taguchi, Takeo

PY - 2005/3/23

Y1 - 2005/3/23

N2 - In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)2 catalyst, N-arylation of ortho-tert-butyl-NH-anilides with 4-nitroiodobenzene proceeds with high enantioselectivity (89-95% ee) to give optically active atropisomeric anilides possessing N-C chiral axis. Furthermore, the intramolecular version of the present catalytic asymmetric N-arylation gave atropisomeric lactams with high optical purity (94-96% ee).

AB - In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)2 catalyst, N-arylation of ortho-tert-butyl-NH-anilides with 4-nitroiodobenzene proceeds with high enantioselectivity (89-95% ee) to give optically active atropisomeric anilides possessing N-C chiral axis. Furthermore, the intramolecular version of the present catalytic asymmetric N-arylation gave atropisomeric lactams with high optical purity (94-96% ee).

UR - http://www.scopus.com/inward/record.url?scp=15744365005&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=15744365005&partnerID=8YFLogxK

U2 - 10.1021/ja042216x

DO - 10.1021/ja042216x

M3 - Article

C2 - 15771484

AN - SCOPUS:15744365005

VL - 127

SP - 3676

EP - 3677

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 11

ER -

Access to Document