Iridium complex-catalyzed enantioselective intramolecular [4+2] cycloaddition of dieneynes

Synlett

Volumn , Issue 10, 2002, Pages 1681-1682

  Shibata, Takanori ^a   Takasaku, Koji ^a   Takesue, Yuri ^a   Hirata, Naohito ^a   Takagi, Kentaro ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Catalysis; Chiral auxiliaries; Cycloadditions; Diels Alder reactions; Iridium

Indexed keywords

2,4 BIS(DIPHENYLPHOSPHINO)PENTANE; ALKADIENE; CYCLOHEXA 1,4 DIENE DERIVATIVE; IRIDIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; CYCLOADDITION; ENANTIOMER; ENANTIOSELECTIVITY; REACTION ANALYSIS;

EID: 0036403387     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34217     Document Type: Article

References (22)

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20. Iridium complex-catalyzed [5+1] cycloaddition has been reported: Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, I.; Ito, Y. J. Org. Chem. 1998, 63, 4.
21. 2 (13.4 mg, 0.02 mmol) in t-BuOAc (1 mL) at 40°C under argon gave a light yellow solution. After addition of a t-BuOAc solution (1 mL) of dieneyne 1a (40.7 mg, 0.205 mmol), the solution was refluxed for 2 h. Solvent was removed under a reduced pressure, then the resulting crude products were purified by thin layer chromatography. Pure 2a was obtained (26.0 mg, 0.131 mmol, 64% yield) and the ee was determined to be 95% by HPLC analysis using a chiral column.
22. Aromatized products 3a-d were also generated (entries 9-12).