Enantioselective Modular Synthesis of 2,4-Disubstituted Cyclopentenones by Iridium-Catalyzed Allylic Alkylation

Classy combo: Together, the asymmetric iridium‐catalyzed allylic alkylation and ruthenium‐catalyzed ring‐closing metathesis lead to an efficient synthesis of chiral cyclopentenones (see scheme). One example is the synthesis of the antitumor agent TEI‐9826 with high enantiomeric purity.

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 45; no. 15; pp. 2466 - 2469
Main Authors Schelwies, Mathias, Dübon, Pierre, Helmchen, Günter
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 03.04.2006
WILEY‐VCH Verlag
Wiley
Subjects
Alkylation
Allyl Compounds - chemistry
allylic substitution
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
cyclopentenones
enantioselectivity
iridium
Iridium - chemistry
Malonates - chemistry
Molecular Structure
Physical Sciences
Propylamines - chemistry
ring-closing metathesis
Science & Technology
Stereoisomerism
enantioselectivity
ASYMMETRIC-SYNTHESIS
SUBSTITUTED CYCLOPENTENONES
cyclopentenones
COMPLEXES
CLOSING METATHESIS
PHOSPHORAMIDITE LIGAND
ring-closing metathesis
iridium
PROSTAGLANDINS
RING
GENERATION
allylic substitution
PHOSPHORUS AMIDITES
CONJUGATE ADDITION
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Summary:Classy combo: Together, the asymmetric iridium‐catalyzed allylic alkylation and ruthenium‐catalyzed ring‐closing metathesis lead to an efficient synthesis of chiral cyclopentenones (see scheme). One example is the synthesis of the antitumor agent TEI‐9826 with high enantiomeric purity.
Bibliography:This work was supported by the Deutsche Forschungsgemeinschaft (SFB 623), the Degussa Stiftung, and the Studienstiftung des deutschen Volkes. We thank Sandra Dreisigacker for her assistance, Dr. K. Ditrich (BASF AG) for enantiomerically pure 1-arylethylamines, and Dr. G. Egri (Reuter Chemischer Apparatebau KG) for a sample of (S)-binol.
istex:D98C3C293DDA59B32F4CA54CD7F0CD4ACE473E99
ArticleID:ANIE200503945
ark:/67375/WNG-JMXBS0T1-C
This work was supported by the Deutsche Forschungsgemeinschaft (SFB 623), the Degussa Stiftung, and the Studienstiftung des deutschen Volkes. We thank Sandra Dreisigacker for her assistance, Dr. K. Ditrich (BASF AG) for enantiomerically pure 1‐arylethylamines, and Dr. G. Egri (Reuter Chemischer Apparatebau KG) for a sample of
binol.
S
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200503945