Diastereoselective Cycloaddition of N-Lithiated Azomethine Ylides to (E)-α,β-Unsaturated Esters Bearing a C2-Symmetric Imidazolidine Chiral Controller

Shuji Kanemasa, Junji Tanaka, Takeshi Hayashi, Hidetoshi Yamamoto, Tosio Sakurai

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68 Citations (Scopus)

Abstract

The 1,3-dipolar cycloaddition of N-metalated azomethine ylides to chiral (E)-3-(1,3-disubstituted 4,5-diphenylimidazolidin-2-yl)propenoates proceeded highly diastereoselectively. The previously unknown absolute configuration of optically pure 1,2-dianilino-1,2-diphenylethane was determined from the absolute configuration of the cycloadducts. What diastereotopic olefin face of the α,β-unsaturated ester was attacked by the ylide was found to depend dramatically upon the nature of N substituents of the chiral controller as well as upon the bulkiness of the ester moiety of the ylide.

Original languageEnglish
Pages (from-to)4473-4481
Number of pages9
JournalJournal of Organic Chemistry
Volume56
Issue number14
DOIs
Publication statusPublished - Jul 1 1991

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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