New Application of Burgess Reagent in its Reaction with Epoxides

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.

amino alcohols - Burgess reagent - epoxides - heterocycles - regioselectivity

References

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2a Burckhardt S. Synlett  2000,  559 

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7 Holton RA. Kim HB. Somoza C. Liang F. Biediger RJ. Boatman PD. Shindo M. Smith CC. Kim S. Nadizadeh H. Suzuki Y. Tao C. Vu P. Tang S. Zhang P. Murthi KK. Gentile LN. Liu JH. J. Am. Chem. Soc.  1994,  116:  1599 

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12a Nicolaou KC. Huang X. Snyder SA. Rao PB. Bella M. Reddy MV. Angew. Chem. Int. Ed.  2002,  41:  834 

12b For further application of Burgess reagent in the reaction with aminoalcohols see: Nicolaou KC. Longbottom DA. Snyder AA. Nalbanadian AZ. Huang X. Angew. Chem. Int. Ed.  2002,  41:  3886 

For recent examples see:

13a Wei L. Lubell WD. Org. Lett.  2000,  2:  2595 

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17

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

18 Katz SJ. Bergmeier SC. Tetrahedron Lett.  2002,  43:  557 

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: [e-mail]