Abstract
The [3+2]-nitrone-mediated cycloaddition reaction of (S )-(-)-4-benzyl-N -methacryloyl-2-oxazolidinone has been applied to the synthesis of highly substituted isoxazolidines with controlled stereochemistry. The absolute configuration of the major diastereoisomer derived from the reaction between N -(p- nitrobenzylidene)methylamine N -oxide and (S )-(-)-4-benzyl-N -methacryloyl-2-oxazolidinone has been deduced from the corresponding X-ray structure.
Key words
chiral auxiliary - nitrones - dipolar cycloaddition reaction - isoxazolidine - isoxazolidinone
References
1 Miyaura N.
Yanagi T.
Suzuki A.
Synth. Commun.
1981,
11:
513
2 Miyaura N.
Suzuki A.
Chem. Rev.
1995,
95:
2457
3a Allin SM.
Shuttleworth SJ.
Tetrahedron Lett.
1996,
37:
8023
3b Green R.
Taylor PJM.
Bull SD.
James TD.
Mahon MF.
Merritt AT.
Tetrahedron: Asymmetry
2003,
14:
2619
3c Chung CWY.
Toy PH.
Tetrahedron: Asymmetry
2004,
15:
387
4 Gefflaut T.
Bauer U.
Airola K.
Koskinen Ari MP.
Tetrahedron: Asymmetry
1996,
7:
3099
5 Tamura O.
Mita N.
Kusaka N.
Suzuki H.
Sakamoto M.
Tetrahedron Lett.
1997,
38:
429
6a Faita G.
Paio A.
Quadrelli P.
Rancati F.
Seneci P.
Tetrahedron Lett.
2000,
41:
1265
6b Desmoni G.
Faita G.
Galbiati A.
Pasini D.
Paio A.
Rancati F.
Tetrahedron: Asymmetry
2002,
13:
333
6c Faita G.
Paio A.
Quadrelli P.
Rancati F.
Seneci P.
Tetrahedron
2001,
57:
8313
7 Tyrrell E.
PhD Thesis
University of Southampton;
UK:
1989.
8a Bouillon J.-P.
Janousek Z.
Viehe HG.
Tinnant B.
Declerq J.-P.
J. Chem. Soc., Perkin Trans. 1
1996,
1853
8b Strauss A.
Otto H.-H.
Helv. Chim. Acta
1997,
80:
1823
9a Basak A.
Bdour HMM.
Bhattacharya G.
Tetrahedron Lett.
1997,
38:
2535
9b Anklam S.
Liebscher J.
Tetrahedron
1998,
54:
6369
10 Dopp D.
Henseleit M.
Chem. Ber.
1982,
115:
798
11a Fornefeld EJ.
Pike AJ.
J. Org. Chem.
1979,
44:
835
11b Ali SA.
Senaratne PA.
Illig CR.
Meckler M.
Tufariello JJ.
Tetrahedron Lett.
1979,
20:
4167
12 Katritzky AR.
Gregory JH.
Xiaohong Z.
J. Chem. Soc., Perkin Trans. 1
1990,
2371
13 Muller P.
Eschenmoser A.
Helv. Chim. Acta
1969,
52:
1823
14a Exner O.
Collect. Czech. Chem. Commun.
1951,
16:
258
14b Robl JA.
Hwu JR.
J. Org. Chem.
1985,
50:
5913
15a Fringuelli F.
Pizzo F.
Taticchi A.
Halls TDG.
Wenkert E.
J. Org. Chem.
1982,
47:
5056
15b Snider BA.
Kirk TC.
J. Am. Chem. Soc.
1983,
105:
2364
15c Smith AB.
Toder BH.
Branca SJ.
Dieter KR.
J. Am. Chem. Soc.
1981,
103:
1996
15d Schnizer D.
Ringe K.
Synlett
1994,
463
15e Whitesell JK.
Matthews SS.
J. Org. Chem.
1977,
42:
3878
16a Kakisawa H.
Kashman Y.
Kusumi T.
Ohtani I.
J. Am. Chem. Soc.
1991,
113:
4092
16b Heumann A.
J. Chem. Soc., Chem. Commun.
1993,
113
16c Riguera R.
Quinoa E.
Seco JM.
Latypov SK.
J. Org. Chem.
1995,
60:
1538
17a Dale JA.
Dull D.
Mosher HS.
J. Org. Chem.
1969,
34:
2543
17b Dale JA.
Mosher HS.
J. Am. Chem. Soc.
1973,
95:
512
18 All compounds provided satisfactory spectral data that were consistent with the assigned structures.
19 Evans DA.
Britton TC.
Ellman JA.
Tetrahedron Lett.
1987,
28:
6141
20 Only one isomer was detectable by 1 H NMR studies on the crude isolate.
21 The enantiomeric excess (92%) was determined by chiral GC using a Supercot α-dex 225 column.
22 Evans DA.
Chapman KT.
Bisaha J.
J. Am. Chem. Soc.
1988,
110:
1238
23 Hamer J.
Macaluso A.
Chem. Rev.
1964,
64:
473
24 Abou-Gharbia M.
Joulke MM.
Synthesis
1977,
318
25 Bjorgo J.
Boyd DR.
Neill DC.
Jennings WB.
J. Chem. Soc., Perkin Trans. 1
1976,
254
