The stereochemistry of the addition of titanium enolates of N- propionyl-oxazolidin-2-ones to 5- and 6-membered N-acyliminium ions

Tetrahedron Letters

Volumn 40, Issue 15, 1999, Pages 2891-2894

  Pilli, Ronaldo A ^a   Alves, Conceicão de Fátima ^a   Böckelmann, Maria Alice ^a   Mascarenhas, Yvonne P ^b   Nery, J Geraldo ^b   Vencato, Ivo ^c  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

^c FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

Author keywords

2 substituted pyrrolidines and piperidines; N acyliminitnn ion; Titanium enolates; amino acid derivatives

Indexed keywords

OXAZOLIDINONE DERIVATIVE; PIPERIDINE DERIVATIVE; TITANIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033537912     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00398-6     Document Type: Article

References (16)

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13. 5: C, 65.65; H, 7.51; N 6.90. Found: C, 65.81; H, 7.45; N, 7.06. X-Ray analysis carried out by Y. P. Mascarenhas and J. G. Nery (Fig 1.). Lists of refined coordinates and esds have been deposited at the Cambridge Crystallographic Data Centre. (Matrix Presented)
14. 5: 450.2155; found: 450.2152. X-Ray analysis carried out by I. Vencato (Fig 2.). Lists of refined coordinates and esds have been deposited at the Cambridge Crystallographic Data Centre. (Matrix Presented)
15. For an unambiguous specification of the steric course of asymmetric syntheses, see: Seebach, D.; Prelog, V. Angew. Chem. Int. Ed. Engl. 1982, 21, 654.
16. 4 and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography on silica gel (9:1 hexane-ethyl acetate as eluent) to afford 3ad (72% yield) and 4ad (8% yield).