The rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates

Bairu Shi; Sandra Merten; David K.Y. Wong; John C.K. Chu; Lok Lok Liu; Sze Kui Lam; Anne Jäger; Wing Tak Wong; Pauline Chiu; Peter Metz

doi:10.1002/adsc.200900695

The rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates

Bairu Shi, Sandra Merten, David K.Y. Wong, John C.K. Chu, Lok Lok Liu, Sze Kui Lam, Anne Jäger, Wing Tak Wong, Pauline Chiu, Peter Metz

Research output: Journal article publication › Journal article › Academic research › peer-review

39 Citations (Scopus)

Abstract

Vinylsulfonates have proved to be excellent dipolarophiles for carbonyl ylides derived from diazoketones in rhodium-catalyzed intramolecular cycloadditions. Polyfunctional substrates, such as 8 and (+)-15, were readily available from hydroxy esters, e.g. 1 and the cyclopenta-1,3-dione 10, respectively, and the resulting polycyclic sultones were formed under mild reaction conditions in high yields with very good diastereoselectivities. A ruthenium-catalyzed asymmetric transfer hydrogenation was found to desymmetrize the meso-cyclopenta-1,3-dione 12 efficiently. KGaA, Weinheim.

Original language	English
Pages (from-to)	3128-3132
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	351
Issue number	18
DOIs	https://doi.org/10.1002/adsc.200900695
Publication status	Published - 1 Jan 2009
Externally published	Yes

Keywords

Asymmetric reduction
Cycloaddition
Domino reactions
Sulfur heterocycles
Transition metal catalysis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

More information

10.1002/adsc.200900695

Cite this

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abstract = "Vinylsulfonates have proved to be excellent dipolarophiles for carbonyl ylides derived from diazoketones in rhodium-catalyzed intramolecular cycloadditions. Polyfunctional substrates, such as 8 and (+)-15, were readily available from hydroxy esters, e.g. 1 and the cyclopenta-1,3-dione 10, respectively, and the resulting polycyclic sultones were formed under mild reaction conditions in high yields with very good diastereoselectivities. A ruthenium-catalyzed asymmetric transfer hydrogenation was found to desymmetrize the meso-cyclopenta-1,3-dione 12 efficiently. KGaA, Weinheim.",

keywords = "Asymmetric reduction, Cycloaddition, Domino reactions, Sulfur heterocycles, Transition metal catalysis",

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T1 - The rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates

AU - Shi, Bairu

AU - Merten, Sandra

AU - Wong, David K.Y.

AU - Chu, John C.K.

AU - Liu, Lok Lok

AU - Lam, Sze Kui

AU - Jäger, Anne

AU - Wong, Wing Tak

AU - Chiu, Pauline

AU - Metz, Peter

PY - 2009/1/1

Y1 - 2009/1/1

N2 - Vinylsulfonates have proved to be excellent dipolarophiles for carbonyl ylides derived from diazoketones in rhodium-catalyzed intramolecular cycloadditions. Polyfunctional substrates, such as 8 and (+)-15, were readily available from hydroxy esters, e.g. 1 and the cyclopenta-1,3-dione 10, respectively, and the resulting polycyclic sultones were formed under mild reaction conditions in high yields with very good diastereoselectivities. A ruthenium-catalyzed asymmetric transfer hydrogenation was found to desymmetrize the meso-cyclopenta-1,3-dione 12 efficiently. KGaA, Weinheim.

AB - Vinylsulfonates have proved to be excellent dipolarophiles for carbonyl ylides derived from diazoketones in rhodium-catalyzed intramolecular cycloadditions. Polyfunctional substrates, such as 8 and (+)-15, were readily available from hydroxy esters, e.g. 1 and the cyclopenta-1,3-dione 10, respectively, and the resulting polycyclic sultones were formed under mild reaction conditions in high yields with very good diastereoselectivities. A ruthenium-catalyzed asymmetric transfer hydrogenation was found to desymmetrize the meso-cyclopenta-1,3-dione 12 efficiently. KGaA, Weinheim.

KW - Asymmetric reduction

KW - Cycloaddition

KW - Domino reactions

KW - Sulfur heterocycles

KW - Transition metal catalysis

UR - http://www.scopus.com/inward/record.url?scp=73349090868&partnerID=8YFLogxK

U2 - 10.1002/adsc.200900695

DO - 10.1002/adsc.200900695

M3 - Journal article

SN - 1615-4150

VL - 351

SP - 3128

EP - 3132

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 18

ER -

The rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates

Abstract

Keywords

ASJC Scopus subject areas

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