Enantio- and Diastereoselective Synthesis of cis-2-Aryl-3-methoxycarbonyl-2,3-dihydrobenzofurans via the Rh(II)-Catalyzed C−H Insertion Process

The enantioselective intramolecular C−H insertion reaction of aryldiazoacetates has been explored with use of dirhodium(II) carboxylate catalysts, which incorporate N-phthaloyl- or N-benzene-fused-phthaloyl-(S)-amino acids as chiral bridging ligands. Dirhodium tetrakis[N-phthaloyl-(S)-tert-leucinate...

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Bibliographic Details
Published inOrganic letters Vol. 4; no. 22; pp. 3887 - 3890
Main Authors Saito, Hiroaki, Oishi, Hiroyuki, Kitagaki, Shinji, Nakamura, Seiichi, Anada, Masahiro, Hashimoto, Shunichi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 31.10.2002
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CATALYTIC ENANTIOSELECTIVE SYNTHESIS
SITE
DIRHODIUM(II)
ACTIVATION
ASYMMETRIC-SYNTHESIS
CARBOXYLATES
LACTONES
CONSTRUCTION
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Summary:The enantioselective intramolecular C−H insertion reaction of aryldiazoacetates has been explored with use of dirhodium(II) carboxylate catalysts, which incorporate N-phthaloyl- or N-benzene-fused-phthaloyl-(S)-amino acids as chiral bridging ligands. Dirhodium tetrakis[N-phthaloyl-(S)-tert-leucinate], Rh2(S-PTTL)4, has proven to be the catalyst of choice for this process, providing exclusively cis-2-aryl-3-methoxycarbonyl-2,3-dihydobenzofurans in up to 94% ee.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0267127