Premium
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 .