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Synthesis 2008(8): 1269-1275
DOI: 10.1055/s-2008-1042944
DOI: 10.1055/s-2008-1042944
PAPER
© Georg Thieme Verlag Stuttgart · New York
A General Organocatalytic Enantioselective Nitrocyclopropanation Reaction
Further Information
Received
21 December 2007
Publication Date:
18 March 2008 (online)
Publication History
Publication Date:
18 March 2008 (online)
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Abstract
A general organocatalytic enantioselective synthesis of nitrocyclopropanes from bromonitromethane and a variety of cyclic and acyclic enones is described.
Key words
asymmetric catalysis - carbocycles - cyclisation - organocatalysis - nitrocyclopropane - tetrazole
- 1
de Meijere A. Chem. Rev. 2003, 103: 931 -
2a
Corey EJ.Achiwa K.Katzenellenbogen JA. J. Am. Chem. Soc. 1969, 91: 4318 -
2b
Donaldson WA. Tetrahedron 2001, 57: 8589 -
2c
Faust R. Angew. Chem. Int. Ed. 2001, 40: 2251 -
2d
Paul VJ.Fenical W. Science 1983, 221: 747 -
2e
Chakraborty TK.Reddy VR. Tetrahedron Lett. 2006, 47: 2099 -
2f
Higgs MD.Mulheirn M. Tetrahedron 1981, 37: 4259 -
2g
Kerr RG.Baker BJ. Nat. Prod. Rep. 1991, 8: 465 -
2h
Williams RM.Fegley GJ. J. Am. Chem. Soc. 1991, 113: 8796 -
2i
Yakambram P.Puranik VG.Gurjar MK. Tetrahedron Lett. 2006, 47: 3781 -
3a
Reichelt A.Martin SF. Acc. Chem. Res. 2006, 39: 433 -
3b
Urman S.Gaus K.Yang Y.Strijowski U.Sewald N.De Pol S.Reiser O. Angew. Chem. Int. Ed. 2007, 46: 3976 -
3c
Koglin N.Zorn C.Beumer R.Cabrele C.Bubert C.Sewald N.Reiser O.Beck-Sickinger A. Angew. Chem. Int. Ed. 2003, 42: 202 - 4
Reichelt A.Gaul C.Frey RR.Kennedy A.Martin SF. J. Org. Chem. 2002, 67: 4062 - 5
Trost BM.Gunzer JL.Dirat O.Rhee YH. J. Am. Chem. Soc. 2002, 124: 10396 - 6
de Meijere A.Wessjohann L. Synlett 1990, 20 - For selected recent publications in this area, see:
-
7a
Rios R.Sundén H.Vesely J.Zaho G.-L.Dziedzic P.Córdova A. Adv. Synth. Catal. 2007, 349: 1028 -
7b
Hartikka A.Arvidsson PI. J. Org. Chem. 2007, 72: 5874 -
7c
Xu Z.-H.Zhu S.-N.Sun X.-L.Tang Y.Dai L.-X. Chem. Commun. 2007, 1960 -
7d
Ferreira VF.Leao RAC.da Silva FdeC.Pinheiro S.Lhoste P.Sinou D. Tetrahedron: Asymmetry 2007, 18: 1217 -
7e
Oudeyer S.Léonel E.Paugam JP.Sulpice-Gaillet C.Nédélec J.-Y. Tetrahedron 2006, 62: 1583 -
7f
Johansson CCC.Bremeyer N.Ley SV.Owen DR.Smith SC.Gaunt MJ. Angew. Chem. Int. Ed. 2006, 45: 6024 -
7g
Du H.Long J.Shi Y. Org. Lett. 2006, 8: 2827 -
7h
Itagaki M.Masumoto K.Suenobu K.Yamamoto Y. Org. Process Res. Dev. 2006, 10: 245 -
7i
McAllister GD.Oswald MF.Paxton RJ.Raw SA.Taylor RJK. Tetrahedron 2006, 62: 6681 -
7j
Mekonnen A.Carlson R. Synthesis 2006, 1657 -
7k
Werner H.Herrerias CI.Glos M.Gissibl A.Fraile JM.Pérez I.Mayoral JA.Reiser O. Adv. Synth. Catal. 2006, 348: 125 -
7l
Lebel H.Marcoux JF.Molinaro C.Charette AB. Chem. Rev. 2003, 103: 977 - 8
Dolbier WR.Battiste MA. Chem. Rev. 2003, 103: 1071 - 9
Oudeyer S.Léonel E.Paugam JP.Sulpice-Gaillet C.Nédélec J.-Y. Tetrahedron 2006, 62: 1583 -
10a
Andres N.Wolf H.Zähner H.Rössner E.Zeek A.König WA.Sinnwell V. Helv. Chim. Acta 1989, 72: 426 -
10b
Rössner E.Zeek A.König WA. Angew. Chem., Int. Ed. Engl. 1990, 29: 64 -
11a
Gootz TD.Brighty KE. Med. Res. Rev. 1996, 16: 433 -
11b
Brighty KE.Castaldi JM. Synlett 1996, 1097 -
12a
Ballini R.Bosica G.Fiorini D.Palmieri A.Petrini M. Chem. Rev. 2005, 105: 933 -
12b
Rosini G.Ballini R. Synthesis 1988, 833 - For selected publications in this area, see:
-
13a
Wurz RP.Charette AB. J. Org. Chem. 2004, 69: 1262 -
13b
Hübner J.Liebscher J.Pätzel M. Tetrahedron 2002, 58: 10485 -
13c
Kumaran G.Kulkarni GH. Synthesis 1995, 1545 -
13d
Yu J.Falck JR.Mioskowski C. J. Org. Chem. 1992, 57: 3757 -
13e
O’Bannon PE.Dailey WP. Tetrahedron 1990, 46: 7341 -
13f
Russell GA.Makosza M.Hershberger J. J. Org. Chem. 1979, 44: 1195 -
13g
Kocôr M.Kroszczynski W. Synthesis 1976, 813 -
13h
O’Bannon PE.Dailey WP. J. Org. Chem. 1990, 55: 353 -
13i
Hübner J.Liebscher J.Pätzel M. Tetrahedron 2002, 58: 10485 -
13j
Snider BB.Che Q. Tetrahedron 2002, 58: 7821 -
13k
Larionov OV.Saveléva T.Kochetkov KA.Ikonnokov NS.Kozhushkov SI.Yufit DS.Howard JAK.Khrustalev VN.Belokon YN.de Meijere A. Eur. J. Org. Chem. 2003, 5: 869 -
14a
Arai S.Nakayama K.Hatano K.Shioiri TS. J. Org. Chem. 1998, 63: 9572 -
14b
McCooey SH.McCabe T.Connon SJ. J. Org. Chem. 2006, 71: 7494 -
14c
Arai S.Nakayama K.Ishida T.Shioiri TS. Tetrahedron Lett. 1999, 40: 4215 -
14d
Ballini R.Fiorini D.Palmieri A. Synlett 2003, 1704 -
14e
Braish TF.Castaldi M.Chan S.Fox DE.Keltonic T.McGarry J.Hawkins JM.Norris T.Rose PR.Sieser JE.Sitter BJ.Watson H. Synlett 1996, 1100 - 15
Hartikka A.Arvidsson PI. Tetrahedron: Asymmetry 2004, 15: 1831 - 16
Torii H.Nakadai M.Ishihara K.Saito S.Yamamoto H. Angew. Chem. Int. Ed. 2004, 43: 1983 -
17a
Cobb AJA.Shaw DM.Ley SV. Synlett 2004, 558 -
17b
Cobb AJA.Longbottom DA.Shaw DM.Ley SV. Chem. Commun. 2004, 1808 -
17c
Cobb AJA.Shaw DM.Longbottom DA.Gold JB.Ley SV. Org. Biomol. Chem. 2005, 3: 84 -
17d
Mitchel CET.Cobb AJA.Ley SV. Synlett 2005, 611 -
17e
Mitchel CET.Brenner SE.Ley SV. Chem. Commun. 2005, 5346 -
17f
Kumarn S.Shaw DM.Longbottom DA.Ley SV. Org. Lett. 2005, 7: 4189 -
17g
Mitchel CET.Brenner SE.García-Fortanet J.Ley SV. Org. Biomol. Chem. 2006, 4: 2039 -
17h
Knudsen KR.Mitchel CET.Ley SV. Chem. Commun. 2006, 66 -
17i
Kumarn S.Shaw DM.Ley SV. Chem. Commun. 2006, 3211 -
17j
Oelke AJ.Kumarn S.Longbottom DA.Ley SV. Synlett 2006, 2548 -
17k
Franckevičius V.Knudsen KR.Ladlow M.Longbottom DA.Ley SV. Synlett 2006, 889 -
17l
Johansson CCC.Bremeyer N.Ley SV.Owen DR.Smith SC.Gaunt MJ. Angew. Chem. Int. Ed. 2006, 45: 6024 -
17m
Kumarn S.Oelke AJ.Shaw DM.Longbottom DA.Ley SV. Org. Biomol. Chem. 2007, 16: 2678 -
18a
Longbottom DA.Franckevičius V.Ley SV. Chimia 2007, 61: 247 -
18b
Longbottom DA.Franckevičius V.Kumarn S.Oelke AJ.Wascholowski V.Ley SV. Aldrichimica Acta 2008, 40: 91 - 19
Hansen HM.Longbottom DA.Ley SV. Chem. Commun. 2006, 4838
References
The reaction between bromonitromethane (3) and morpholine (4) may lead to the formation of the product 22 (Figure [2] ), which is confirmed by 1H and 13C NMR spectroscopy. MS analysis was unsuccessful.
Figure 2 Product formed from the reaction of bromonitromethane (3) and morpholine (4)
One recrystallisation gives material of ÷99% ee.