Efficient catalysis of Nazarov cyclization using a cationic iridium complex possessing adjacent labile coordination sites

Journal of the American Chemical Society

Volumn 126, Issue 22, 2004, Pages 6864-6865

  Janka, Mesfin ^a   He, Wei ^a   Frontier, Alison J ^a   Eisenberg, Richard ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COORDINATION COMPOUND; IRIDIUM COMPLEX; KETONE DERIVATIVE; LEWIS ACID; NATURAL PRODUCT;

AROMATIZATION; ARTICLE; BINDING AFFINITY; BINDING SITE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; CONROTATORY CYCLIZATION; CYCLIZATION; ENANTIOSELECTIVITY; ISOMERISM; NAZAROV CYCLIZATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 3042813853     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049643v     Document Type: Article

References (18)

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10. p-p = 4.8 Hz, 1P, cis to CO).
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12. p-c = 123 Hz, 1P, cis to CO).
13. p-p = 4.7 Hz, 1P, cis to CO).
14. -1.
15. Each β-keto ester product 7 was isolated as a single regio- and stereoisomer with a trans relationship of the α and β substituents on the former vinyl electrophile and characterized as reported in ref 3.
16. Substrate 9 does not cyclize when treated with 1 even with increased catalyst loading and longer reaction time at high temperature.
17. p-p = 6.0 Hz, 1P, cis to CO).
18. p-p = 5.1 Hz, 1P, cis to CO).