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Synlett 2003(9): 1247-1252
DOI: 10.1055/s-2003-40356
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

New Application of Burgess Reagent in its Reaction with Epoxides

Uwe Rinnera, David R. Adamsa, Maria L. dos Santosb, Khalil A. Abbouda, Tomas Hudlicky*a
a Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
Fax: +1(352)8461203; e-Mail: hudlicky@chem.ufl.edu;
b Instituto de Química, Universidade de Brasília, Brasília, Distrito Federal, 70.910-900 Brazil
Further Information

Publication History

Received 5 May 2003
Publication Date:
30 June 2003 (online)

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Abstract

Burgess reagent, (methoxycarbonylsulfamoyl)triethyl­ammonium hydroxide, usually used for the dehydration of secondary or tertiary alcohols, was successfully employed in the formation of sulfamidates from the corresponding epoxides. It was further shown that the same reaction with aromatic epoxides results in the formation of seven-membered ring systems.

Key words

amino alcohols - Burgess reagent - epoxides - heterocycles - regioselectivity

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17

We thank Professor K. C. Nicolaou for providing the NMR/IR data for 16 and 19.

19

All NMR data were obtained on a Varian 300 MHz instrument and chemical shifts are reported in ppm in respect to TMS (0 ppm). 8: 1H NMR (CDCl3, 300 MHz) δ 5.00 (m, 1 H), 4.22 (m, 1 H), 3.90 (s, 3 H), 2.33 (m, 2 H), 1.45-1.85 (m, 5 H), 1.16-1.33 (m, 2 H); 13: 1H NMR (CDCl3, 300 MHz) δ 4.79 (m, 1 H), 4.15 (dd, J = 9.7 Hz, 5.6 Hz, 1 H), 3.84 (s, 3 H), 3.66 (t, J = 9.7 Hz), 1.81-1.95 (m, 1 H), 1.65-1.78 (m, 1 H), 1.25-1.45 (m, 4 H), 0.87 (t, J = 6.7 Hz, 3 H); 15: 1H NMR (CDCl3, 300 MHz) δ 7.36-7.47 (m, 5 H), 6.15 (dd, J = 10.7 Hz, 3.6 Hz, 1 H), 4.62 (dd, J = 12.6 Hz, 10.5 Hz, 1 H), 4.52 (dd, J = 12.6 Hz, 3.6 Hz, 1 H), 3.93 (s, 3 H); 18: 1H NMR (CDCl3, 300 MHz), δ 7.85-7.91 (m, 4 H), 7.43-7.60 (m, 3 H), 6.32 (dd, J = 10.8 Hz, 3.3 Hz, 1 H), 4.73 (dd, J = 12.9 Hz, 11.1 Hz, 1 H), 4.61 (dd, J = 12.3 Hz, 3.6 Hz, 1 H), 3.96 (s, 3 H).

20

Homochiral aminoalcohol i has been used to prepare the bicyclic derivative ii, conversion of ii to the asymmetric version of the Burgess reagent and its reactions with meso and racemic epoxides are under investigation (Scheme [7] ).

21

All queries regarding X-ray data should be directed to Khalil A. Abboud. E-mail: abboud@chem.ufl.edu