Iron-catalyzed olefin carbometalation [15]

Journal of the American Chemical Society

Volumn 122, Issue 5, 2000, Pages 978-979

  Nakamura, Masaharu ^a   Hirai, Atsushi ^a   Nakamura, Eiichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; IRON;

ALKYLATION; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; LETTER; REACTION ANALYSIS;

EID: 0034624407     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983066r     Document Type: Letter

References (36)

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19. 3 afforded 3 in less than 2% yield under the same conditions.
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32. A tridentate amine, N,N,N′,N″,N″-pentamethyldiethylenetriamine, exerted the same effects. Interestingly enough, monodentate amines (triethyl-N,N-methylpyrroridine and N-methylmorphorine) produced a racemic product.
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35. 2 = H) (0.219 g, 64% yield). Chiral GLC analysis showed that the (R)-product was obtained as a major enantiomer with 90% ee. In a smaller scale (0.4 mmol) experiment, the carbozincation product was obtained in 88% yield with 89% ee (Table 2, entry 3).
36. Chiral ligands such as (-)-sparteine, PyBOX, bis-oxazoline (BOX), DIOP, and CHIRAPHOS were ineffective either to promote the reaction or to effect enantioselective reaction.