UNEXPECTED STEREOSELECTIVITY OF INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION CAUSED BY THE PRESENCE OF FLUORINE ATOM

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作者
IHARA, M
KAWABUCHI, T
TOKUNAGA, Y
FUKUMOTO, K
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O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Intramolecular 1,3-dipolar cycloaddition of nitrones (11; R = Me, Et, and Bn) bearing one fluorine atom at the quaternary alpha-position produced two diastereoisomers of bicyclic isoxazolidines (12) and (13). It was revealed that the stereochemical outcome was considerably influenced by the presence of fluorine atom.
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页码:97 / 100
页数:4
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