Enantioselective 1,3-dipolar cycloaddition of nitrones catalyzed by optically active cationic cobalt(III) complexes

Organic Letters

Volumn 4, Issue 15, 2002, Pages 2457-2460

  Mita, Tsuyoshi ^a   Ohtsuki, Natsuki ^a   Ikeno, Taketo ^a   Yamada, Tohru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001660873     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026079p     Document Type: Article

References (49)

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43. 1,3-Dipolar cycloaddition of 3-chlorobenzylidenphenylamine N-oxide proceeded in 76% yield with 98% endo selectivity and 22% ee (endo) using the cationic cobalt(III) catalyst 1c.
44. Reaction of 2,3-dichlorobenzylidenphenylamine-N-oxide (2e) and methacrolein in the presence of cobalt catalysts 1e at -40 °C afforded the corresponding cycloadduct quantitatively in 94/6 regio selectivity and with complete endo selectivity with 78% ee. See the Supporting Information.
45. Crystallographic data for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC 186919.
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48. The cycloadduct 4d was debrominated by treatment with n-BuLi at -78 °C to afford 4a without loss of optically purity. HPLC analysis of these compounds revealed that the absolute configuration of the debrominated product was the same as that of 4a afforded by complex 1e. Therefore, it is reasonable to consider that a halide on the ortho position could have little influence on enantioselectivity.
49. Recently, it was reported that ortho-substituted benzaldehyde derivatives displayed particularly good reactivity and enantioselectivity relative to other substituted derivatives in the hetero-ene reactions with tridentate Schiff base chromium(III) complexes. Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2882.