Silver-catalyzed carbon dioxide incorporation and rearrangement on propargylic derivatives

Satoshi Kikuchi, Shunsuke Yoshida, Yuudai Sugawara, Wataru Yamada, Hau Man Cheng, Kohei Sekine, Izumi Iwakura, Taketo Ikeno, Tohru Yamada

Research output: Contribution to journalArticle

84 Citations (Scopus)

Abstract

A silver/DBU catalyst system was developed for the effective synthesis of cyclic carbonate and oxazolidinone from the reaction of CO2 with propargylic alcohols and propargylic amines, respectively, in high yields under mild conditions. It was found that the [3,3]-sigmatropic MeyerSchuster- type rearrangement of the propargylic alcohol was mediated by CO2 in DMF to afford the corresponding α,β-unsaturated carbonyl compounds in high yields. The silver salt combined with the chiral Schiff base ligand could be applied to enantioselective chemical CO2 incorporation into various bispropargylic alcohols to produce the corresponding cyclic carbonate in high yields with high enantioselectivity. The absolute configuration was determined by VCD spectroscopy as well as by X-ray analysis. These products were found to be active for the aminolysis reaction to afford the corresponding carbamate derivatives in high yields without any loss of optical purity.

Original languageEnglish
Pages (from-to)698-717
Number of pages20
JournalBulletin of the Chemical Society of Japan
Volume84
Issue number7
DOIs
Publication statusPublished - 2011

Fingerprint

Silver
Carbon Dioxide
Carbonates
Alcohols
Derivatives
Oxazolidinones
Carbonyl compounds
Carbamates
Schiff Bases
Enantioselectivity
X ray analysis
Amines
Salts
Spectroscopy
Ligands
Catalysts

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Silver-catalyzed carbon dioxide incorporation and rearrangement on propargylic derivatives. / Kikuchi, Satoshi; Yoshida, Shunsuke; Sugawara, Yuudai; Yamada, Wataru; Cheng, Hau Man; Sekine, Kohei; Iwakura, Izumi; Ikeno, Taketo; Yamada, Tohru.

In: Bulletin of the Chemical Society of Japan, Vol. 84, No. 7, 2011, p. 698-717.

Research output: Contribution to journalArticle

Kikuchi, S, Yoshida, S, Sugawara, Y, Yamada, W, Cheng, HM, Sekine, K, Iwakura, I, Ikeno, T & Yamada, T 2011, 'Silver-catalyzed carbon dioxide incorporation and rearrangement on propargylic derivatives', Bulletin of the Chemical Society of Japan, vol. 84, no. 7, pp. 698-717. https://doi.org/10.1246/bcsj.20110078
Kikuchi, Satoshi ; Yoshida, Shunsuke ; Sugawara, Yuudai ; Yamada, Wataru ; Cheng, Hau Man ; Sekine, Kohei ; Iwakura, Izumi ; Ikeno, Taketo ; Yamada, Tohru. / Silver-catalyzed carbon dioxide incorporation and rearrangement on propargylic derivatives. In: Bulletin of the Chemical Society of Japan. 2011 ; Vol. 84, No. 7. pp. 698-717.
@article{8432cd75ba074719a0dda24e283025cf,
title = "Silver-catalyzed carbon dioxide incorporation and rearrangement on propargylic derivatives",
abstract = "A silver/DBU catalyst system was developed for the effective synthesis of cyclic carbonate and oxazolidinone from the reaction of CO2 with propargylic alcohols and propargylic amines, respectively, in high yields under mild conditions. It was found that the [3,3]-sigmatropic MeyerSchuster- type rearrangement of the propargylic alcohol was mediated by CO2 in DMF to afford the corresponding α,β-unsaturated carbonyl compounds in high yields. The silver salt combined with the chiral Schiff base ligand could be applied to enantioselective chemical CO2 incorporation into various bispropargylic alcohols to produce the corresponding cyclic carbonate in high yields with high enantioselectivity. The absolute configuration was determined by VCD spectroscopy as well as by X-ray analysis. These products were found to be active for the aminolysis reaction to afford the corresponding carbamate derivatives in high yields without any loss of optical purity.",
author = "Satoshi Kikuchi and Shunsuke Yoshida and Yuudai Sugawara and Wataru Yamada and Cheng, {Hau Man} and Kohei Sekine and Izumi Iwakura and Taketo Ikeno and Tohru Yamada",
year = "2011",
doi = "10.1246/bcsj.20110078",
language = "English",
volume = "84",
pages = "698--717",
journal = "Bulletin of the Chemical Society of Japan",
issn = "0009-2673",
publisher = "Chemical Society of Japan",
number = "7",

}

TY - JOUR

T1 - Silver-catalyzed carbon dioxide incorporation and rearrangement on propargylic derivatives

AU - Kikuchi, Satoshi

AU - Yoshida, Shunsuke

AU - Sugawara, Yuudai

AU - Yamada, Wataru

AU - Cheng, Hau Man

AU - Sekine, Kohei

AU - Iwakura, Izumi

AU - Ikeno, Taketo

AU - Yamada, Tohru

PY - 2011

Y1 - 2011

N2 - A silver/DBU catalyst system was developed for the effective synthesis of cyclic carbonate and oxazolidinone from the reaction of CO2 with propargylic alcohols and propargylic amines, respectively, in high yields under mild conditions. It was found that the [3,3]-sigmatropic MeyerSchuster- type rearrangement of the propargylic alcohol was mediated by CO2 in DMF to afford the corresponding α,β-unsaturated carbonyl compounds in high yields. The silver salt combined with the chiral Schiff base ligand could be applied to enantioselective chemical CO2 incorporation into various bispropargylic alcohols to produce the corresponding cyclic carbonate in high yields with high enantioselectivity. The absolute configuration was determined by VCD spectroscopy as well as by X-ray analysis. These products were found to be active for the aminolysis reaction to afford the corresponding carbamate derivatives in high yields without any loss of optical purity.

AB - A silver/DBU catalyst system was developed for the effective synthesis of cyclic carbonate and oxazolidinone from the reaction of CO2 with propargylic alcohols and propargylic amines, respectively, in high yields under mild conditions. It was found that the [3,3]-sigmatropic MeyerSchuster- type rearrangement of the propargylic alcohol was mediated by CO2 in DMF to afford the corresponding α,β-unsaturated carbonyl compounds in high yields. The silver salt combined with the chiral Schiff base ligand could be applied to enantioselective chemical CO2 incorporation into various bispropargylic alcohols to produce the corresponding cyclic carbonate in high yields with high enantioselectivity. The absolute configuration was determined by VCD spectroscopy as well as by X-ray analysis. These products were found to be active for the aminolysis reaction to afford the corresponding carbamate derivatives in high yields without any loss of optical purity.

UR - http://www.scopus.com/inward/record.url?scp=79960422223&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79960422223&partnerID=8YFLogxK

U2 - 10.1246/bcsj.20110078

DO - 10.1246/bcsj.20110078

M3 - Article

AN - SCOPUS:79960422223

VL - 84

SP - 698

EP - 717

JO - Bulletin of the Chemical Society of Japan

JF - Bulletin of the Chemical Society of Japan

SN - 0009-2673

IS - 7

ER -