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, Ferenc Sztaricskai

Research output: Contribution to journalArticle

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of '2-amino-1-phenyl-propan-1,3-diol as chiral auxiliary. Application in the synthesis of cis 3-phthalimido-4-styryl-2-azetidinones'. Together they form a unique fingerprint.

  • Cite this