2-amino-1-phenyl-propan-1,3-diol as chiral auxiliary. Application in the synthesis of cis 3-phthalimido-4-styryl-2-azetidinones

Tamas E. Gunda, F. Sztaricskai

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21 Citations (Scopus)

Abstract

3,4-cis3,4-cis-1-N-(1'-phenyl-1',3'-dihydroxy-2'-propyl)-3-phthalimido-4 -styrylazetidinones were obtained in optically pure form by chiral Staudinger reaction. The cis-α/β-ratio could be influenced by the protective groups of the diol moiety. Removal of the chiral auxiliarity could be accomplished by direct oxidation, or by previous double bond formation, thus the 2-amino-1-phenyl-propan-1,3-diol can be regarded to a generally useful chiral auxiliary.

Original languageEnglish
Pages (from-to)7985-7998
Number of pages14
JournalTetrahedron
Volume53
Issue number23
DOIs
Publication statusPublished - Jun 9 1997

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2-azetidinone

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

2-amino-1-phenyl-propan-1,3-diol as chiral auxiliary. Application in the synthesis of cis 3-phthalimido-4-styryl-2-azetidinones. / Gunda, Tamas E.; Sztaricskai, F.

In: Tetrahedron, Vol. 53, No. 23, 09.06.1997, p. 7985-7998.

Research output: Contribution to journalArticle

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