Asymmetric Pauson-Khand-type reactions of 1,6-enynes using formaldehyde as a carbonyl source by cooperative dual rhodium catalysis

Takuma Furusawa; Tsumoru Morimoto; Keiichi Ikeda; Hiroki Tanimoto; Yasuhiro Nishiyama; Kiyomi Kakiuchi; Nakcheol Jeong

doi:10.1016/j.tet.2014.12.038

Asymmetric Pauson-Khand-type reactions of 1,6-enynes using formaldehyde as a carbonyl source by cooperative dual rhodium catalysis

Takuma Furusawa
, Tsumoru Morimoto^*
, Keiichi Ikeda
, Hiroki Tanimoto
, Yasuhiro Nishiyama
, Kiyomi Kakiuchi
, Nakcheol Jeong

^*Corresponding author for this work

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

32 Citations (Scopus)

Abstract

A dual neutral-cationic rhodium(I)-catalyzed Pauson-Khand-type reaction using formaldehyde as a carbonyl source is described. The simultaneous use of neutral rhodium(I) and cationic rhodium(I) complexes is required for efficient cooperative catalysis, which involves the neutral rhodium(I)-catalyzed decarbonylation of formaldehyde and the cationic rhodium(I)-catalyzed cyclocarbonylation of 1,6-enynes using the resulting carbonyl moiety.

Original language	English
Pages (from-to)	875-881
Number of pages	7
Journal	Tetrahedron
Volume	71
Issue number	5
DOIs	https://doi.org/10.1016/j.tet.2014.12.038
Publication status	Published - 2015 Feb 4

Bibliographical note

Funding Information:
This work was supported partly by Grants-in-Aid for Scientific Research on Innovative Area ‘Molecular Activation Directed toward Straightforward Synthesis’ from the Ministry of Education, Culture, Sports, Science and Technology, Japan (No. 25105737 ). We thank Ms. Yoshiko Nishikawa and Mr. Kazuo Fukuda for the HRMS measurements.

Publisher Copyright:
© 2014 Elsevier Ltd. All rights reserved.

Keywords

Asymmetric Pauson-Khand reaction
Decarbonylation
Dual catalysis
Enyne
Formaldehyde

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2014.12.038

Cite this

@article{d6b110e475394901bf10689c3d9e6f9b,

title = "Asymmetric Pauson-Khand-type reactions of 1,6-enynes using formaldehyde as a carbonyl source by cooperative dual rhodium catalysis",

abstract = "A dual neutral-cationic rhodium(I)-catalyzed Pauson-Khand-type reaction using formaldehyde as a carbonyl source is described. The simultaneous use of neutral rhodium(I) and cationic rhodium(I) complexes is required for efficient cooperative catalysis, which involves the neutral rhodium(I)-catalyzed decarbonylation of formaldehyde and the cationic rhodium(I)-catalyzed cyclocarbonylation of 1,6-enynes using the resulting carbonyl moiety.",

keywords = "Asymmetric Pauson-Khand reaction, Decarbonylation, Dual catalysis, Enyne, Formaldehyde",

author = "Takuma Furusawa and Tsumoru Morimoto and Keiichi Ikeda and Hiroki Tanimoto and Yasuhiro Nishiyama and Kiyomi Kakiuchi and Nakcheol Jeong",

note = "Funding Information: This work was supported partly by Grants-in-Aid for Scientific Research on Innovative Area {\textquoteleft}Molecular Activation Directed toward Straightforward Synthesis{\textquoteright} from the Ministry of Education, Culture, Sports, Science and Technology, Japan (No. 25105737 ). We thank Ms. Yoshiko Nishikawa and Mr. Kazuo Fukuda for the HRMS measurements. Publisher Copyright: {\textcopyright} 2014 Elsevier Ltd. All rights reserved.",

year = "2015",

month = feb,

day = "4",

doi = "10.1016/j.tet.2014.12.038",

language = "English",

volume = "71",

pages = "875--881",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "5",

}

TY - JOUR

T1 - Asymmetric Pauson-Khand-type reactions of 1,6-enynes using formaldehyde as a carbonyl source by cooperative dual rhodium catalysis

AU - Furusawa, Takuma

AU - Morimoto, Tsumoru

AU - Ikeda, Keiichi

AU - Tanimoto, Hiroki

AU - Nishiyama, Yasuhiro

AU - Kakiuchi, Kiyomi

AU - Jeong, Nakcheol

N1 - Funding Information: This work was supported partly by Grants-in-Aid for Scientific Research on Innovative Area ‘Molecular Activation Directed toward Straightforward Synthesis’ from the Ministry of Education, Culture, Sports, Science and Technology, Japan (No. 25105737 ). We thank Ms. Yoshiko Nishikawa and Mr. Kazuo Fukuda for the HRMS measurements. Publisher Copyright: © 2014 Elsevier Ltd. All rights reserved.

PY - 2015/2/4

Y1 - 2015/2/4

N2 - A dual neutral-cationic rhodium(I)-catalyzed Pauson-Khand-type reaction using formaldehyde as a carbonyl source is described. The simultaneous use of neutral rhodium(I) and cationic rhodium(I) complexes is required for efficient cooperative catalysis, which involves the neutral rhodium(I)-catalyzed decarbonylation of formaldehyde and the cationic rhodium(I)-catalyzed cyclocarbonylation of 1,6-enynes using the resulting carbonyl moiety.

AB - A dual neutral-cationic rhodium(I)-catalyzed Pauson-Khand-type reaction using formaldehyde as a carbonyl source is described. The simultaneous use of neutral rhodium(I) and cationic rhodium(I) complexes is required for efficient cooperative catalysis, which involves the neutral rhodium(I)-catalyzed decarbonylation of formaldehyde and the cationic rhodium(I)-catalyzed cyclocarbonylation of 1,6-enynes using the resulting carbonyl moiety.

KW - Asymmetric Pauson-Khand reaction

KW - Decarbonylation

KW - Dual catalysis

KW - Enyne

KW - Formaldehyde

UR - https://www.scopus.com/pages/publications/84920746902

U2 - 10.1016/j.tet.2014.12.038

DO - 10.1016/j.tet.2014.12.038

M3 - Article

AN - SCOPUS:84920746902

SN - 0040-4020

VL - 71

SP - 875

EP - 881

JO - Tetrahedron

JF - Tetrahedron

IS - 5

ER -

Asymmetric Pauson-Khand-type reactions of 1,6-enynes using formaldehyde as a carbonyl source by cooperative dual rhodium catalysis

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this