Improvement of TADDOLate-TiCl2-Catalyzed 1,3-Dipolar Nitrone Cycloaddition by Substitution of the Oxazolidinone Auxiliary of the Alkene with Succinimide

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2471-2477

  Jensen, Kim B ^a   Gothelf, Kurt V ^a   Hazell, Rita G ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000619069     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962214y     Document Type: Article

References (74)

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59. In an attempt to account for the endo-selectivity in the 1,3-dipolar cycloaddition reaction of nitrone 2a with N-crotonoylsuccinimide (11a) a series of ab initio calculations have been performed using a 3-21G* basis set. The geometry of both 11a-s-cis (total energy = -583.970 au) and 11a-s-trans have been optimized, and it has been found that the former is 5 kcal/mol more stable than the latter. The dihedral angle of the alkene plane relative to the succinimide plane of 11a-s-trans is 24°. A comparison of the approach of 2a to 11a-s-cis leading to endo-12a and exo-12a reveals that for the latter a steric repulsion between the C-phenyl substituent of the nitrone and one of the carbonyls of the succinimide group may account for the former reaction path.
60. We have also tried to use N-crotonoylsuccinimide (11a) as the substrate m Ti-TADDOLate catalyzed Diels-Alder reactions with cyclopentadiene as the reagent, but the Diels-Alder product was formed with low diastereoselectivity.
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