Regio- and stereoselective opening of phenyloxirane by lithium azide: A direct access to 2-azido-1-phenylethanol

Synlett

Volumn 1991, Issue 6, 1991, Pages 403-404

  Guy, Alain ^a   Dubuffet, Thierry ^a,b   Doussot, Joël ^a   Godefroy Falguieres, Annie ^a  

^a Bioinformatique et Chimie Moléculaire   (France)

^b INSTITUT DE RECHERCHES SERVIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013645443     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1991-20742     Document Type: Article

References (13)

1. Present adress : Institut de Recherches Servier (IDRS) 11, rue des Moulineaux 92150 SURESNES
2. Gorzinski Smith, J. Synthesis, 1984,629
3. Chini, M.; Crotti, P.; Macchia, F. Tetrahedron Lett., 1990,31,5641
4. Sutowardoyo, K. ; Emziane, M. ; Sinou, D. Tetrahedron Lett., 1989, 30, 4673 and references cited therein
5. Effets de sels en chimie organique et organometallique ; Loupy, A. ; Tchoubar, B. Bordas, Paris 1988
6. Hu, Y. ; Uno, M. ; Harada, A. ; Takahashi, S. Chem. Lett., 1990,797
7. Iqbal, J. ; Pandey, A. Tetrahedron Lett, 1990,31, 575
8. Yamada, J. ; Yumoto, M. ; Yamamoto, Y. Tetrahedron Lett., 1989, 30,4255
9. Poelsche, E. ; Hickel, A. ; H6nig, H. ; Seufer-Wasserthal, P. J. Org. Chem., 1990, 55,1749
10. Mukhopadhyay, T. ; Seebach, D. Helv. Chim. Acta, 1982, 65,385
11. In a typical procedure, lithium azide (0.06 g ; 1.2 mmol) was added to a solution of phenyloxirane 1 (0.120 g ; 1 mmol) in 1 ml of dry HMPA. The suspension was heated at 60C during 18 h. After cooling the yellow reaction mixture obtained was poured into 10 ml of water and then the mixture was extracted with Et20. Evaporation of the extracts afforded 0.130 g (75 %) of a mixture of the two regioisomers which were separated by flash chromatography on silica gel (15-40 u,m), with : heptane/ethyl acetate 70/30 as the eluant
12. lH and 13C NMR spectra of the two regioisomers are in accordance with the literature data 7
13. The ee > 98 % was determined by lH NMR spectra and HPLC analysis of the MTPA esters 2: [ai20 =-99(C = 3,CH2Cl2)