Controlling π-Facial Diastereoselectivity in the 1,3-Dipolar Cycloadditions of Diazomethane to Chiral Pentenoates and Furanones: Enantioselective Stereodivergent Syntheses of Cyclopropane Hydroxy Acids and Didehydro Amino Acids

Marta Martín-Vilà, Neuh Hanafi, José M. Jiménez, Angel Alvarez-Larena, Joan F. Piniella, Vicenç Branchadell, Antonio Oliva, Rosa M. Ortuño

Research output: Contribution to journalArticleResearchpeer-review

29 Citations (Scopus)

Abstract

The title compounds have been synthesized in both enantiomeric forms and in good overall yields by using D-glyceraldehyde as the single chiral precursor. The efficiency and usefulness of the synthetic routes have been secured by performing controlled manipulations of the functional groups and by highly stereoselective transformations, namely Wittig-Horner condensations and cyclopropanations. Cyclopropane derivatives have been synthesized through 1,3-dipolar cycloaddition of diazomethane to chiral pentenoates or furanones obtained, in turn, from D-glyceraldehyde. Syn/ anti stereochemistry of the cycloadducts has been unequivocally assigned and rationalized. Since π-facial diastereoselectivity involved in these cycloadditions is the opposite for cyclic and open- chain structures, enantiomeric series of products can be derived.
Original languageEnglish
Pages (from-to)3581-3589
JournalJournal of Organic Chemistry
Volume63
DOIs
Publication statusPublished - 29 May 1998

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