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DOI: 10.1055/s-2003-40356
New Application of Burgess Reagent in its Reaction with Epoxides
Publication History
Publication Date:
30 June 2003 (online)
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
- 1
Burgess EM.Penton HR.Taylor EA. J. Am. Chem. Soc. 1970, 92: 5224 - For recent reviews about Burgess reagent see:
-
2a
Burckhardt S. Synlett 2000, 559 -
2b
Lamberth C. J. Prakt. Chem. 2000, 342: 518 - 3
Rigby JH.Mateo ME. J. Am. Chem. Soc. 1997, 119: 12655 - 4
Rigby JH.Kirova-Snover M. Tetrahedron Lett. 1997, 38: 8153 - 5
Dolle RE.Nicolaou KC. J. Am . Chem. Soc. 1985, 107: 1691 - 6
Daniewski AR.Wokulicj PM.Uskokovic MR. J. Org. Chem. 1992, 57: 7133 - 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 -
8a
Nemoto H.Kubota Y.Yamamoto Y. J. Org. Chem. 1990, 55: 4515 -
8b
Claremon DA.Phillips BT. Tetrahedron Lett. 1988, 29: 2155 - 9
Creedon SM.Crowley HC.McCarthy DG. J. Chem. Soc., Perkin Trans. 1 1998, 1015 - 10
Burgess EM.Penton HR.Taylor EA.Williams WM. Org. Synth. 1977, 56: 40 - 11
Wipf P.Venkatrman S. Tetrahedron Lett. 1996, 37: 4659 -
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 -
13b
Boulton LT.Stock HT.Raphy J.Horwell DC. J. Chem. Soc. Perkin Trans. 1 1999, 1421 -
13c
Ok D.Fisher MH.Wyvratt MJ.Meinke PT. Tetrahedron Lett. 1999, 40: 3831 - 14
Kim BM.Sharpless KB. Tetrahedron Lett. 1989, 30: 655 - 15
Rinner U.Siengalewicz P.Hudlicky T. Org. Lett. 2002, 4: 115 - 16
Nagel AA.DiBrino J.Vincent LA.Retsema JA. J. Med. Chem. 1982, 25: 881 - 18
Katz SJ.Bergmeier SC. Tetrahedron Lett. 2002, 43: 557
References
We thank Professor K. C. Nicolaou for providing the NMR/IR data for 16 and 19.
19All 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).
20Homochiral 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] ).
21All queries regarding X-ray data should be directed to Khalil A. Abboud. E-mail: abboud@chem.ufl.edu