Highly stereoselective hydroformylation of a (2R)-2-tert-butyl-Δ4-1,3-oxazoline derivative

L. Kollár, Pétér Sándor

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Methyl (2R)-2-tert-butyl-Δ4-1,3-oxazoline-3-carboxylate has been hydroformylated to give methyl (2R,4R)-2-tert-butyl-4-formyloxazolidine-3-carboxylate and methyl (2R,5S)-2-tert-butyl-5-formyl-oxazolidine-3-carboxylate with up to 99% diastereoselectivities in homogeneous transition-metal-catalysed reactions. A mixture of regioisomers was formed in the presence of rhodium catalysts. Platinum catalysts gave almost exclusively methyl (2R,5S)-2-tert-butyl-5-formyl-oxazolidine-3-carboxylate. The formyl products obtained are important intermediates for the synthesis of homochiral amino acid derivatives of considerable synthetic value.

Original languageEnglish
Pages (from-to)257-259
Number of pages3
JournalJournal of Organometallic Chemistry
Volume445
Issue number1-2
DOIs
Publication statusPublished - Feb 23 1993

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Hydroformylation
carboxylates
Derivatives
Rhodium
Catalysts
Platinum
Transition metals
Amino acids
Metals
Amino Acids
catalysts
rhodium
amino acids
platinum
transition metals
oxazolidine
synthesis
products

ASJC Scopus subject areas

  • Biochemistry
  • Chemical Engineering (miscellaneous)
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Science (miscellaneous)
  • Materials Chemistry

Cite this

Highly stereoselective hydroformylation of a (2R)-2-tert-butyl-Δ4-1,3-oxazoline derivative. / Kollár, L.; Sándor, Pétér.

In: Journal of Organometallic Chemistry, Vol. 445, No. 1-2, 23.02.1993, p. 257-259.

Research output: Contribution to journalArticle

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N2 - Methyl (2R)-2-tert-butyl-Δ4-1,3-oxazoline-3-carboxylate has been hydroformylated to give methyl (2R,4R)-2-tert-butyl-4-formyloxazolidine-3-carboxylate and methyl (2R,5S)-2-tert-butyl-5-formyl-oxazolidine-3-carboxylate with up to 99% diastereoselectivities in homogeneous transition-metal-catalysed reactions. A mixture of regioisomers was formed in the presence of rhodium catalysts. Platinum catalysts gave almost exclusively methyl (2R,5S)-2-tert-butyl-5-formyl-oxazolidine-3-carboxylate. The formyl products obtained are important intermediates for the synthesis of homochiral amino acid derivatives of considerable synthetic value.

AB - Methyl (2R)-2-tert-butyl-Δ4-1,3-oxazoline-3-carboxylate has been hydroformylated to give methyl (2R,4R)-2-tert-butyl-4-formyloxazolidine-3-carboxylate and methyl (2R,5S)-2-tert-butyl-5-formyl-oxazolidine-3-carboxylate with up to 99% diastereoselectivities in homogeneous transition-metal-catalysed reactions. A mixture of regioisomers was formed in the presence of rhodium catalysts. Platinum catalysts gave almost exclusively methyl (2R,5S)-2-tert-butyl-5-formyl-oxazolidine-3-carboxylate. The formyl products obtained are important intermediates for the synthesis of homochiral amino acid derivatives of considerable synthetic value.

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