Solvent effects on the asymmetric Pauson-Khand-type reaction by rhodium

Yun Hee Choi; Jaesung Kwak; Nakcheol Jeong

doi:10.1016/j.tetlet.2009.08.060

Solvent effects on the asymmetric Pauson-Khand-type reaction by rhodium

Yun Hee Choi, Jaesung Kwak, Nakcheol Jeong

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

20 Citations (Scopus)

Abstract

The reaction efficiency and enantioselectivity of an asymmetric Pauson-Khand-type reaction catalyzed by cationic rhodium are heavily dependent on the solvent. Coordinating solvents, such as THF, provide a faster reaction and better stereoselectivity than non-coordinating solvents, such as toluene. These beneficial effects can be attributed to a significant increase in the more reactive catalytic species of [Rh(bisphosphane ligand)^*(solvent)_n]⁺ (3) than of [Rh(bisphosphine ligand)^*CO(solvent)]⁺(4) and [Rh(bisphosphine ligand)*(CO)₂]⁺ (5) in a coordinating solvent.

Original language	English
Pages (from-to)	6068-6071
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	44
DOIs	https://doi.org/10.1016/j.tetlet.2009.08.060
Publication status	Published - 2009 Nov 4

Bibliographical note

Funding Information:
This study was supported by the Korea Science and Engineering Foundation (KOSEF) Grant (No. R01-2007-000-10534-0 ) and by the Korea Research Foundation Grant ( KRF-2007-313-C00414 ) funded by Korean Government (MOST and MOEHRD).

Keywords

Chiral THF derivatives
Enantioselective
Pauson-Khand reaction
Rhodium

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2009.08.060

Cite this

@article{0f4264f5d2214331bf7599e07f4545d1,

title = "Solvent effects on the asymmetric Pauson-Khand-type reaction by rhodium",

abstract = "The reaction efficiency and enantioselectivity of an asymmetric Pauson-Khand-type reaction catalyzed by cationic rhodium are heavily dependent on the solvent. Coordinating solvents, such as THF, provide a faster reaction and better stereoselectivity than non-coordinating solvents, such as toluene. These beneficial effects can be attributed to a significant increase in the more reactive catalytic species of [Rh(bisphosphane ligand)*(solvent)n]+ (3) than of [Rh(bisphosphine ligand)*CO(solvent)]+(4) and [Rh(bisphosphine ligand)*(CO)2]+ (5) in a coordinating solvent.",

keywords = "Chiral THF derivatives, Enantioselective, Pauson-Khand reaction, Rhodium",

author = "Choi, {Yun Hee} and Jaesung Kwak and Nakcheol Jeong",

note = "Funding Information: This study was supported by the Korea Science and Engineering Foundation (KOSEF) Grant (No. R01-2007-000-10534-0 ) and by the Korea Research Foundation Grant ( KRF-2007-313-C00414 ) funded by Korean Government (MOST and MOEHRD). ",

year = "2009",

month = nov,

day = "4",

doi = "10.1016/j.tetlet.2009.08.060",

language = "English",

volume = "50",

pages = "6068--6071",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "44",

}

TY - JOUR

T1 - Solvent effects on the asymmetric Pauson-Khand-type reaction by rhodium

AU - Choi, Yun Hee

AU - Kwak, Jaesung

AU - Jeong, Nakcheol

N1 - Funding Information: This study was supported by the Korea Science and Engineering Foundation (KOSEF) Grant (No. R01-2007-000-10534-0 ) and by the Korea Research Foundation Grant ( KRF-2007-313-C00414 ) funded by Korean Government (MOST and MOEHRD).

PY - 2009/11/4

Y1 - 2009/11/4

N2 - The reaction efficiency and enantioselectivity of an asymmetric Pauson-Khand-type reaction catalyzed by cationic rhodium are heavily dependent on the solvent. Coordinating solvents, such as THF, provide a faster reaction and better stereoselectivity than non-coordinating solvents, such as toluene. These beneficial effects can be attributed to a significant increase in the more reactive catalytic species of [Rh(bisphosphane ligand)*(solvent)n]+ (3) than of [Rh(bisphosphine ligand)*CO(solvent)]+(4) and [Rh(bisphosphine ligand)*(CO)2]+ (5) in a coordinating solvent.

AB - The reaction efficiency and enantioselectivity of an asymmetric Pauson-Khand-type reaction catalyzed by cationic rhodium are heavily dependent on the solvent. Coordinating solvents, such as THF, provide a faster reaction and better stereoselectivity than non-coordinating solvents, such as toluene. These beneficial effects can be attributed to a significant increase in the more reactive catalytic species of [Rh(bisphosphane ligand)*(solvent)n]+ (3) than of [Rh(bisphosphine ligand)*CO(solvent)]+(4) and [Rh(bisphosphine ligand)*(CO)2]+ (5) in a coordinating solvent.

KW - Chiral THF derivatives

KW - Enantioselective

KW - Pauson-Khand reaction

KW - Rhodium

UR - http://www.scopus.com/inward/record.url?scp=70149117734&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2009.08.060

DO - 10.1016/j.tetlet.2009.08.060

M3 - Article

AN - SCOPUS:70149117734

SN - 0040-4039

VL - 50

SP - 6068

EP - 6071

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 44

ER -

Solvent effects on the asymmetric Pauson-Khand-type reaction by rhodium

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this