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Synthesis 2008(18): 3009-3011
DOI: 10.1055/s-2008-1067251
DOI: 10.1055/s-2008-1067251
PSP
© Georg Thieme Verlag
Stuttgart ˙ New York
DBU-Catalyzed Addition Reactions of Sulfonylimidates
Further Information
Received
14 July 2008
Publication Date:
04 September 2008 (online)
Publication History
Publication Date:
04 September 2008 (online)
Abstract
Sulfonylimidates react with various types of N-protected imines in the presence of a catalytic amount of DBU to afford β-aminosulfonylimidates in high yields and high anti-selectivities. The experimental procedure is described in detail.
Key words
addition reaction - imine - catalysis - sulfonylimidate - direct reaction
-
1a
Harada S.Handa S.Matsunaga S.Shibasaki M. Angew. Chem. Int. Ed. 2005, 44: 4439 -
1b
Morimoto H.Wiedeman SH.Yamaguchi A.Harada S.Chien Z.Matsunaga S.Shibasaki M. Angew. Chem. Int. Ed. 2006, 45: 3146 -
1c
Marigo M.Kjarsgaard K.Juhl K.Gathergood N.Jørgensen KA. Chem. Eur. J. 2003, 9: 2359 -
1d
Hamashima Y.Sasamoto N.Hotta D.Somei H.Umebayashi N.Sodeoka M. Angew. Chem. Int. Ed. 2005, 44: 1549 -
1e
Bernardi L.Gothelf AS.Hazell RG.Jørgensen KA. J. Org. Chem. 2003, 68: 2583 -
1f
Ooi T.Kameda M.Fujii JI.Maruoka K. Org. Lett. 2004, 6: 2397 -
1g
Kobayashi J.Yamashita Y.Kobayashi S. Chem. Lett. 2005, 34: 268 -
1h
Salter MM.Kobayashi J.Shimizu Y.Kobayashi S. Org. Lett. 2006, 8: 3533 - 2
Matsubara R.Berthiol F.Kobayashi S. J. Am. Chem. Soc. 2008, 130: 1804 -
3a
Kupfer R.Nagel M.Würthwein E.-U.Allmann R. Chem. Ber. 1985, 118: 3089 -
3b
Walter W.Krohn J. Liebigs Ann. Chem. 1973, 443 -
3c
Yoo EJ.Bae I.Cho SH.Han H.Chang S. Org. Lett. 2006, 8: 1347 ; and references cited therein -
5a
Kanazawa AM.Denis J.-N.Greene AE. J. Am. Chem. Soc. 1994, 59: 1238 -
5b
Vishwakarma LC.Stringer OD.Davis FA. Org. Synth. 1987, 66: 203 -
5c
Love BE.Raje PS.Williams TC. Synlett 1994, 493 -
5d
Hodous BL.Fu GC. J. Am. Chem. Soc. 2002, 124: 1578 -
5e
Hagiwara E.Fujii A.Sodeoka M. J. Am. Chem. Soc. 1998, 120: 2474
References
Thorough evaporation of the solvents provided the imidate HCl salt (a solid). The solidification of imidate salt could be encouraged by keeping it under argon at -20 ˚C. The exposure to air should be avoided as this salt readily absorbs moisture to form a gum-like solid, from which it was found to be difficult to remove the starting materials.