Chiral relay effects influence the facial selectivity of N-alkylated 5- phenylmorpholin-2-one enolates

Tetrahedron Asymmetry

Volumn 9, Issue 9, 1998, Pages 1483-1487

  Bull, Steven D ^a   Davies, Stephen G ^a   Fox, David J ^a   Sellers, Thomas G R ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

MORPHOLINE DERIVATIVE;

ARTICLE; CHIRALITY; CIS TRANS ISOMERISM; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0032496128     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00095-0     Document Type: Article

References (7)

1. S. D. Bull, S. G. Davies, S. W. Epstein, J. V. A. Ouzman, Chem. Commun., 1998, 659.
2. J. F. Dellaria Jr., B. D. Santarsiero, Tetrahedron Lett., 1988, 47, 6079; J. F. Dellaria Jr., B. D. Santarsiero, J. Org. Chem., 1989, 54, 3916.
3. J. F. Dellaria Jr., B. D. Santarsiero, Tetrahedron Lett., 1988, 47, 6079; J. F. Dellaria Jr., B. D. Santarsiero, J. Org. Chem., 1989, 54, 3916.
4. Molecular modelling calculations were carried out using CS Chem3D Pro™ (CambridgeSoft Corp., 875 Massachusetts Ave., Cambridge, Massachusetts 02139 USA).
5. H. Benhaoua, F. Texier, L. Toupet, R. Carrié, Tetrahedron, 1988, 44, 1117.
6. Indirect evidence on the conformation of an N-methyl group morpholinone was gained from examining the X-ray crystal structure of 11 (Fig. 9) which clearly revealed a methyl group occupying a pseudo-axial position; C. Agami, D. Bihan, C. Puchot-Kadouri, Tetrahedron, 1996, 52, 9079.
7. We found that substitution of LHMDS for NaHMDS gave better yields of the monobenzylated auxiliaries.