Catalytic Enantioselective Tandem Carbonyl Ylide Formation/1,3‐Dipolar Cycloaddition Reactions of α‐Diazo Ketones with Aromatic Aldehydes using Dirhodium( II ) Tetrakis[ N ‐benzene‐fused‐phthaloyl‐( S )‐valinate] | Zendy

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

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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‐fused‐phthaloyl‐( S )‐valinate]

Author(s) -

Tsutsui Hideyuki,

Shimada Naoyuki,

Abe Takumi,

Anada Masahiro,

Nakajima Makoto,

Nakamura Seiichi,

Nambu Hisanori,

Hashimoto Shunichi

Publication year - 2007

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.200600591

Subject(s) - chemistry , cycloaddition , ylide , diazo , enantioselective synthesis , aldehyde , catalysis , azomethine ylide , benzene , medicinal chemistry , aryl , 1,3 dipolar cycloaddition , organic chemistry , alkyl

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 1‐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 .

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