A switch of enantiofacial selectivities using designed similar chiral ligands in zirconium-catalyzed asymmetric aza Diels-Alder reactions

Journal of Organic Chemistry

Volumn 64, Issue 12, 1999, Pages 4220-4221

  Kobayashi, Shu ^a   Kusakabe, Ken ichi ^b   Komiyama, Susumu ^b   Ishitani, Haruro ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

1 NAPHTHOL; BENZENE; TOLUENE; ZIRCONIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; CONFORMATIONAL TRANSITION; ENANTIOMER; STEREOCHEMISTRY;

EID: 0033546377     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9902300     Document Type: Article

References (35)

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30. When 10 mol % of the catalyst was used, chemical yield and enantioselectivity decreased (81%, 77% ee).
31. Experimental details are shown in the Supporting Information.
32. 5. See the Supporting Information.
33. It was assumed that formation of 7 was slow and incomplete at 23 °C due to the bulky 3,3′-phenyl groups of 3.
34. One of the reviewers pointed out that the tert-butoxy group of the catalyst would play a major role in shielding one or the other side of the imino moiety. Actually, we performed the reaction using a catalyst having an n-propoxy group instead of a tert-butoxy group and found that the selectivity was slightly decreased. Further investigations are needed to clarify the precise transition states. We that the reviewer for the fruitful suggestions.
35. For the assumed transition states of the reactions using 1, see refs 4a and 6. See also: Ishitani, H.; Kitazawa, T.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 2161.