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

Department of Chemistry

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

17 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

Keywords

Chiral THF derivatives
Enantioselective
Pauson-Khand reaction
Rhodium

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2009.08.060

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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). ",

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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

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SN - 0040-4039

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 44

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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