Chiral cyclopentadiene-mediated approach to enantioselective heterobimetallic Pauson-Khand reactions

Ramon Rios; Sergi Paredes; Miquel A. Pericàs; Albert Moyano

doi:10.1016/j.jorganchem.2004.09.046

Chiral cyclopentadiene-mediated approach to enantioselective heterobimetallic Pauson-Khand reactions

Ramon Rios
, Sergi Paredes
, Miquel A. Pericàs
, Albert Moyano

Chemistry

Facultat QuIImica, Univ. B.

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

20 Scopus citations

Abstract

When the dicobalt(hexacarbonyl) complex of N-(2-butynoyl)-4,4- dimethyloxazolidinone (1) is treated with chiral cyclopentadienyl (tricarbonyl)molybdenum anions, pairs of diastereomeric heterobimetallic (Co-Mo) complexes are obtained. In one instance, the two diastereomers have been separated by chromatography and they have been reacted with norbornadiene; each diastereomer leads with virtually complete stereocontrol to a single enantiomer of the endo Pauson-Khand cycloadduct 5.

Original language	British English
Pages (from-to)	358-362
Number of pages	5
Journal	Journal of Organometallic Chemistry
Volume	690
Issue number	2
DOIs	https://doi.org/10.1016/j.jorganchem.2004.09.046
State	Published - 17 Jan 2005

Keywords

Alkynes
Asymmetric synthesis
Chiral cyclopentadienes
Cobalt
Molybdenum
Pauson-Khand reactions

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10.1016/j.jorganchem.2004.09.046

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@article{a2d77542601f4b1e858f90d081a15212,

title = "Chiral cyclopentadiene-mediated approach to enantioselective heterobimetallic Pauson-Khand reactions",

abstract = "When the dicobalt(hexacarbonyl) complex of N-(2-butynoyl)-4,4- dimethyloxazolidinone (1) is treated with chiral cyclopentadienyl (tricarbonyl)molybdenum anions, pairs of diastereomeric heterobimetallic (Co-Mo) complexes are obtained. In one instance, the two diastereomers have been separated by chromatography and they have been reacted with norbornadiene; each diastereomer leads with virtually complete stereocontrol to a single enantiomer of the endo Pauson-Khand cycloadduct 5.",

keywords = "Alkynes, Asymmetric synthesis, Chiral cyclopentadienes, Cobalt, Molybdenum, Pauson-Khand reactions",

author = "Ramon Rios and Sergi Paredes and Peric{\`a}s, \{Miquel A.\} and Albert Moyano",

note = "Funding Information: Financial support of this work by the Ministerio de Ciencia y Tecnolog{\'ı}a (DGI, project BQU2003-03426) and by the Direcci{\'o} General de Recerca, Generalitat de Catalunya (2001SGR 00050) is gratefully acknowledged.",

year = "2005",

month = jan,

day = "17",

doi = "10.1016/j.jorganchem.2004.09.046",

language = "British English",

volume = "690",

pages = "358--362",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier B.V.",

number = "2",

}

TY - JOUR

T1 - Chiral cyclopentadiene-mediated approach to enantioselective heterobimetallic Pauson-Khand reactions

AU - Rios, Ramon

AU - Paredes, Sergi

AU - Pericàs, Miquel A.

AU - Moyano, Albert

N1 - Funding Information: Financial support of this work by the Ministerio de Ciencia y Tecnologı́a (DGI, project BQU2003-03426) and by the Direcció General de Recerca, Generalitat de Catalunya (2001SGR 00050) is gratefully acknowledged.

PY - 2005/1/17

Y1 - 2005/1/17

N2 - When the dicobalt(hexacarbonyl) complex of N-(2-butynoyl)-4,4- dimethyloxazolidinone (1) is treated with chiral cyclopentadienyl (tricarbonyl)molybdenum anions, pairs of diastereomeric heterobimetallic (Co-Mo) complexes are obtained. In one instance, the two diastereomers have been separated by chromatography and they have been reacted with norbornadiene; each diastereomer leads with virtually complete stereocontrol to a single enantiomer of the endo Pauson-Khand cycloadduct 5.

AB - When the dicobalt(hexacarbonyl) complex of N-(2-butynoyl)-4,4- dimethyloxazolidinone (1) is treated with chiral cyclopentadienyl (tricarbonyl)molybdenum anions, pairs of diastereomeric heterobimetallic (Co-Mo) complexes are obtained. In one instance, the two diastereomers have been separated by chromatography and they have been reacted with norbornadiene; each diastereomer leads with virtually complete stereocontrol to a single enantiomer of the endo Pauson-Khand cycloadduct 5.

KW - Alkynes

KW - Asymmetric synthesis

KW - Chiral cyclopentadienes

KW - Cobalt

KW - Molybdenum

KW - Pauson-Khand reactions

UR - https://www.scopus.com/pages/publications/11844305004

U2 - 10.1016/j.jorganchem.2004.09.046

DO - 10.1016/j.jorganchem.2004.09.046

M3 - Article

AN - SCOPUS:11844305004

SN - 0022-328X

VL - 690

SP - 358

EP - 362

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 2

ER -

Chiral cyclopentadiene-mediated approach to enantioselective heterobimetallic Pauson-Khand reactions

Abstract

Keywords

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