Homochiral oxazolidin-2-ones and imidazolidin-2-ones by tandem nucleophilic addition-conjugate addition

Marco Ciclosi, Cristiana Fava, Roberta Galeazzi, Mario Orena, Maria Eugenia González-Rosende, José Sepúlveda-Arques

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Treatment of both primary alcohols 1a,b and secondary amines 1c,d, tethered to a Michael acceptor with (R)-phenylethyl isocyanate in the presence of DBU gave in good yield and high stereoselection diastereomeric mixtures of oxazolidin-2-ones 2a,b and 3a,b and imidazolidin-2-ones 2c,d and 3c,d, respectively. The cyclisation reaction was studied computationally by ab initio quantum mechanical methods. The observed stereoselectivity was explained on the basis of the different stability of both anions and transition states leading to 2a and 3a, respectively. The usefulness of the method was proven by conversion of 2a into the enantiomerically pure bioactive amino acid 5.

Original languageEnglish
Pages (from-to)1937-1943
Number of pages7
JournalTetrahedron: Asymmetry
Volume15
Issue number12
DOIs
Publication statusPublished - Jun 21 2004

Fingerprint

Oxazolidinones
Stereoselectivity
isocyanates
Cyclization
activity (biology)
Amines
Anions
amino acids
Amino acids
amines
alcohols
Alcohols
Negative ions
anions
Amino Acids
ethylene urea
phenylethyl isocyanate

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Homochiral oxazolidin-2-ones and imidazolidin-2-ones by tandem nucleophilic addition-conjugate addition. / Ciclosi, Marco; Fava, Cristiana; Galeazzi, Roberta; Orena, Mario; González-Rosende, Maria Eugenia; Sepúlveda-Arques, José.

In: Tetrahedron: Asymmetry, Vol. 15, No. 12, 21.06.2004, p. 1937-1943.

Research output: Contribution to journalArticle

Ciclosi, Marco ; Fava, Cristiana ; Galeazzi, Roberta ; Orena, Mario ; González-Rosende, Maria Eugenia ; Sepúlveda-Arques, José. / Homochiral oxazolidin-2-ones and imidazolidin-2-ones by tandem nucleophilic addition-conjugate addition. In: Tetrahedron: Asymmetry. 2004 ; Vol. 15, No. 12. pp. 1937-1943.
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AU - González-Rosende, Maria Eugenia

AU - Sepúlveda-Arques, José

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