Catalytic enantioselective tandem carbonyl ylide formation/1,3 dipolar cycloaddition reactions of α-diazo ketones with aromatic aldehydes using dirhodium(II) tetrakis[N-benzene-fusedphthaloyl- (S)-valinate]

Hideyuki Tsutsui; Naoyuki Shimada; Takumi Abe; Masahiro Anada; Makoto Nakajima; Seiichi Nakamura; Hisanori Nambu; Shunichi Hashimoto

doi:10.1002/adsc.200600591

Catalytic enantioselective tandem carbonyl ylide formation/1,3 dipolar cycloaddition reactions of α-diazo ketones with aromatic aldehydes using dirhodium(II) tetrakis[N-benzene-fusedphthaloyl- (S)-valinate]

Hideyuki Tsutsui, Naoyuki Shimada, Takumi Abe, Masahiro Anada, Makoto Nakajima, Seiichi Nakamura, Hisanori Nambu, Shunichi Hashimoto

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

51 Citations (Scopus)

Abstract

The first successful example of the enantioselective intermolecular 1,3-dipolar cycloaddition of a chiral dirhodium(II) catalyst-associated carbonyl ylide with an aromatic aldehyde dipolarophile is described. The tandem carbonyl ylide formation/cycloaddition reactions of l-diazo-5-aryl-2,5-pentanediones with aromatic aldehydes using dirhodium(II) tetrakis[N-benzene-fused-phthaloyl- (S)-valinate] as a catalyst provide exclusively exo cycloadducts in up to 92% ee.

Original language	English
Pages (from-to)	521-526
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	349
Issue number	4-5
DOIs	https://doi.org/10.1002/adsc.200600591
Publication status	Published - Mar 2007
Externally published	Yes

Keywords

1,3-dipolar cycloaddition
A-diazo ketones
Aldehydes
Asymmetric catalysis
Carbonyl ylides
Chiral dirhodium(II) carboxylates

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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Tsutsui, H., Shimada, N., Abe, T., Anada, M., Nakajima, M., Nakamura, S., Nambu, H., & Hashimoto, S. (2007). Catalytic enantioselective tandem carbonyl ylide formation/1,3 dipolar cycloaddition reactions of α-diazo ketones with aromatic aldehydes using dirhodium(II) tetrakis[N-benzene-fusedphthaloyl- (S)-valinate]. Advanced Synthesis and Catalysis, 349(4-5), 521-526. https://doi.org/10.1002/adsc.200600591

Catalytic enantioselective tandem carbonyl ylide formation/1,3 dipolar cycloaddition reactions of α-diazo ketones with aromatic aldehydes using dirhodium(II) tetrakis[N-benzene-fusedphthaloyl- (S)-valinate]. / Tsutsui, Hideyuki; Shimada, Naoyuki; Abe, Takumi et al.
In: Advanced Synthesis and Catalysis, Vol. 349, No. 4-5, 03.2007, p. 521-526.

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

Tsutsui, H, Shimada, N, Abe, T, Anada, M, Nakajima, M, Nakamura, S, Nambu, H & Hashimoto, S 2007, 'Catalytic enantioselective tandem carbonyl ylide formation/1,3 dipolar cycloaddition reactions of α-diazo ketones with aromatic aldehydes using dirhodium(II) tetrakis[N-benzene-fusedphthaloyl- (S)-valinate]', Advanced Synthesis and Catalysis, vol. 349, no. 4-5, pp. 521-526. https://doi.org/10.1002/adsc.200600591

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title = "Catalytic enantioselective tandem carbonyl ylide formation/1,3 dipolar cycloaddition reactions of α-diazo ketones with aromatic aldehydes using dirhodium(II) tetrakis[N-benzene-fusedphthaloyl- (S)-valinate]",

abstract = "The first successful example of the enantioselective intermolecular 1,3-dipolar cycloaddition of a chiral dirhodium(II) catalyst-associated carbonyl ylide with an aromatic aldehyde dipolarophile is described. The tandem carbonyl ylide formation/cycloaddition reactions of l-diazo-5-aryl-2,5-pentanediones with aromatic aldehydes using dirhodium(II) tetrakis[N-benzene-fused-phthaloyl- (S)-valinate] as a catalyst provide exclusively exo cycloadducts in up to 92% ee.",

keywords = "1,3-dipolar cycloaddition, A-diazo ketones, Aldehydes, Asymmetric catalysis, Carbonyl ylides, Chiral dirhodium(II) carboxylates",

author = "Hideyuki Tsutsui and Naoyuki Shimada and Takumi Abe and Masahiro Anada and Makoto Nakajima and Seiichi Nakamura and Hisanori Nambu and Shunichi Hashimoto",

year = "2007",

month = mar,

doi = "10.1002/adsc.200600591",

language = "English",

volume = "349",

pages = "521--526",

journal = "Advanced Synthesis and Catalysis",

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AU - Tsutsui, Hideyuki

AU - Shimada, Naoyuki

AU - Abe, Takumi

AU - Anada, Masahiro

AU - Nakajima, Makoto

AU - Nakamura, Seiichi

AU - Nambu, Hisanori

AU - Hashimoto, Shunichi

PY - 2007/3

Y1 - 2007/3

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AB - The first successful example of the enantioselective intermolecular 1,3-dipolar cycloaddition of a chiral dirhodium(II) catalyst-associated carbonyl ylide with an aromatic aldehyde dipolarophile is described. The tandem carbonyl ylide formation/cycloaddition reactions of l-diazo-5-aryl-2,5-pentanediones with aromatic aldehydes using dirhodium(II) tetrakis[N-benzene-fused-phthaloyl- (S)-valinate] as a catalyst provide exclusively exo cycloadducts in up to 92% ee.

KW - 1,3-dipolar cycloaddition

KW - A-diazo ketones

KW - Aldehydes

KW - Asymmetric catalysis

KW - Carbonyl ylides

KW - Chiral dirhodium(II) carboxylates

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Catalytic enantioselective tandem carbonyl ylide formation/1,3 dipolar cycloaddition reactions of α-diazo ketones with aromatic aldehydes using dirhodium(II) tetrakis[N-benzene-fusedphthaloyl- (S)-valinate]

Abstract

Keywords

ASJC Scopus subject areas

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