Highly enantioselective 1,3-dipolar cycloaddition reactions of 2-benzopyrylium-4-olate catalyzed by chiral Lewis acids

Journal of the American Chemical Society

Volumn 124, Issue 50, 2002, Pages 14836-14837

  Suga, Hiroyuki ^a   Inoue, Kei ^a   Inoue, Shuichi ^a   Kakehi, Akikazu ^a  

^a SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LEWIS ACID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CYCLOADDITION; ENANTIOMER;

ALDEHYDES; MESYLATES; METALS, RARE EARTH; OXAZOLES; PYRIDINES; PYRUVATES; SCANDIUM; STEREOISOMERISM; YTTRIUM;

EID: 0037132621     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028676c     Document Type: Article

References (21)

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18. We have previously reported that asymmetric induction was observed in a ytterbium tris-1,1′-binaphthyl-2,2′-diyl phosphonate-catalyzed cycloaddition of a carbonyl ylide with moderate enantioselectivity (up to 52% ee). See ref 8b.
19. 3 (10 mol %) without Pybox ligands, the reactions proceeded with high exoselectivity (exo:endo = 94:6 or 93:7).
20. 3 did not exhibit asymmetric induction. These results indicate that bidentate coordination of a dipolarophile to the catalyst, as a Lewis acid, is important for this reaction.
21. 3; endo:exo = 85:15).