Syntheses of iminolyxitols via tandem reduction-alkenylation of O'Donnell's Schiff bases

Hossein Razavi, Robin L Polt

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The concise enantioselective synthesis of iminolyxitol glycosidase inhibitors starting from benzophenone imines of D-serine and L-alanine esters is very efficient. The reductive-alkenylation of the Schiff bases followed by substrate-directed dihydroxylation and amino dehydration gave the polyhydroxylated pyrrolidines in excellent overall yields (19.6% for 3 → 8. 9.9% for 2 → 13.).

Original languageEnglish (US)
Pages (from-to)3371-3374
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number21
DOIs
StatePublished - May 21 1998

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Alkenylation
Pyrrolidines
Imines
Schiff Bases
Glycoside Hydrolases
Dehydration
Alanine
Serine
Esters
Substrates
benzophenone

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Syntheses of iminolyxitols via tandem reduction-alkenylation of O'Donnell's Schiff bases. / Razavi, Hossein; Polt, Robin L.

In: Tetrahedron Letters, Vol. 39, No. 21, 21.05.1998, p. 3371-3374.

Research output: Contribution to journalArticle

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