Reagent-controlled diastereoselectivity in aziridination of alkenes by chiral 3-acetoxyamino-3,4-dihydroquinazolin-4-ones: 1'-(t- butyldimethylsilyloxy)ethyl as the chiral 2-substituent on the quinazolinone

Tetrahedron Letters

Volumn 37, Issue 29, 1996, Pages 5179-5182

  Atkinson, Robert S ^a   Coogan, Michael P ^a   Lochrie, Ian S T ^a  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AZIRIDINE; QUINAZOLINONE DERIVATIVE; REAGENT; SILANE DERIVATIVE; STYRENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL STRUCTURE; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0030586111     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01055-6     Document Type: Article

References (13)

1. 1. R.S. Atkinson, M.J. Grimshire and B.J. Kelly, Tetrahedron, 1989, 45, 2875.
2. 2. R.S. Atkinson, J. Fawcett, D.R. Russell and P.J. Williams, J. Chem. Soc., Chem. Commun., 1994, 2031.
3. 3. R.S. Atkinson and B.J. Kelly, J. Chem. Soc., Perkin Trans. 1, 1989, 1515.
4. 4. R.S. Atkinson and G. Tughan, J. Chem. Soc., Perkin Trans. 1, 1987, 2803.
5. 5. R.S. Atkinson and P.J, Williams, J. Chem. Soc., Perkin Trans. II, 1996, 205.
6. 6. R.S. Atkinson, M.P. Coogan and I.S.T. Lochrie, Chem. Commun., 1996, 789.
7. -3). Details of both the above structures have been deposited at the Cambridge Crystallographic Data Centre, Lensfield Road, Cambridge.
8. 8. B. Gung, J.P. Melnick, M.A. Wolf and A. King, J. Org. Chem., 1995, 60, 1947; B. Gung and M.B. Francis, Tetrahedron Lett., 1995, 36, 2579 and refs. therein.
9. 8. B. Gung, J.P. Melnick, M.A. Wolf and A. King, J. Org. Chem., 1995, 60, 1947; B. Gung and M.B. Francis, Tetrahedron Lett., 1995, 36, 2579 and refs. therein.
10. 9. R.S. Atkinson and J.R. Malpass, J. Chem. Soc., Perkin Trans. 1, 1977, 2242.
11. 10. The quinazolinone ring and C-O bond are not perfectly eclipsed: the torsion angle between C-O and C=N bonds is 12.32°.
12. 11. The crystal structure of a aziridine diastereoisomer from reaction of Q*NHOAc 3 with cyclohexen-1-ol also shows the same conformational preferences for the chiral 2-substituent (R.S. Atkinson and P.J. Williams, unpublished work).
13. 12. The 3-aminoquinazolinone precursor of 12 was synthesised from (S)-t-leucine (W.T. Gattrell unpublished work) by a method analogous to that used for the preparation of the precursor of Q*NHOAc 3 (R.S. Atkinson, B.J. Kelly and J. Williams, Tetrahedron, 1992, 48, 7713).