Abstract
We describe the first efficient oxidation of homoallylic and homopropargylic alcohols to the corresponding very sensitive and unstable b,g-unsaturated aldehydes by using the Dess-Martin periodinane with a new neutral and anhydrous extraction protocol.
Key words
b,g-ethylenic aldehyde - b,g-acetylenic aldehyde - oxidation - Dess-Martin periodinane - DMP
References
1 Durand S.
Parrain J.-L.
Santelli M.
J. Chem. Soc., Perkin Trans. 1
2000,
253
2 Corey EJ.
Wright SW.
J. Org. Chem.
1990,
55:
1670
3 Michaud, S.; Wavrin, L.; Viala, J. Synth. Commun. 2002 , in press.
4a Viala J.
Santelli M.
J. Org. Chem.
1988,
53:
6121
4b Viala J.
Labaudinière R.
J. Org. Chem.
1993,
58:
1280
4c Sandri J.
Viala J.
Synthesis
1995,
271
4d Sandri J.
Viala J.
J. Org. Chem.
1995,
60:
6627
4e Michaud S.
Viala J.
Tetrahedron
1999,
55:
3019
4f Sha W.
Salomon RG.
J. Org. Chem.
2000,
65:
5315
5a Corey EJ.
Lansbury PT.
J. Am. Chem. Soc.
1983,
105:
4093
5b Neumann C.
Boland W.
Helv. Chim. Acta
1990,
73:
754
5c Taber DF.
You K.
J. Org. Chem.
1995,
60:
139
5d Saha G.
Basu MK.
Kim S.
Jung Y.-J.
Adiyaman Y.
Adiyaman M.
Powell WS.
Fitzgerald GA.
Rokach J.
Tetrahedron Lett.
1999,
40:
7179
5e Taber DF.
Jiang Q.
J. Org. Chem.
2001,
66:
1876
6a Jain SC.
Dussourd DE.
Conner WE.
Eisner T.
Guerrero A.
Meinwald J.
J. Org. Chem.
1983,
48:
2266
6b Baxter AD.
Binns F.
Javed T.
Roberts SM.
Sadler P.
Scheinmann F.
Wakefield BJ.
Lynch M.
J. Chem. Soc., Perkin Trans. 1
1986,
889
6c Stoller A.
Mioskowski C.
Millet J.
Sepulchre C.
Bellamy F.
Tetrahedron Lett.
1990,
35:
5035
6d Khanapure SP.
Manna S.
Rokach J.
Murphy RC.
Wheelan P.
Powell WS.
J. Org. Chem.
1995,
60:
1806
6e Han L.
Razdan RK.
Tetrahedron Lett.
1998,
39:
771
7a Begley MJ.
Pattenden G.
Smithies A.
Tapolczay D.
Walter DS.
J. Chem. Soc., Perkin Trans. 1
1996,
21
7b Saha G.
Khanapure SP.
Powell WS.
Rokach J.
Tetrahedron Lett.
2000,
41:
6313
7c Van den Nieuwendijk AMCH.
Kriek NMAJ.
Brussee J.
Van Boom JH.
Van der Gen A.
Eur. J. Org. Chem.
2000,
3683
7d Aïssa C.
Dhimane A.-L.
Malacria M.
Synlett
2000,
1585
7e Commeiras L.
Santelli M.
Parrain J.-L.
Org. Lett.
2001,
3:
1713
8 Narkunan K.
Shiu L.-H.
Liu R.-S.
Synlett
2000,
1300
9 Treilhou M.
Fauve A.
Pougny J.-R.
Promé J.-C.
Veschambre H.
J. Org. Chem.
1992,
57:
3203
10 DMP: 1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H )-one.
11 Larock RC.
Comprehensive Organic Reactions
VCH Publishers, Inc.;
New York:
1989.
p.604-616
12a Dess DB.
Martin JC.
J. Org. Chem.
1983,
48:
4155
12b Dess DB.
Martin JC.
J. Am. Chem. Soc.
1991,
113:
7277
13a Bastiaans HMM.
van der Baan JL.
Ottenheijm HCJ.
J. Org. Chem.
1997,
62:
3880
13b Bose DS.
Narsaiah AV.
Synth. Commun.
1999,
29:
937
13c Durand T.
Guy A.
Henry O.
Vidal O.
Rossi J.-C.
Rivalta C.
Valagussa A.
Chiabrando C.
Eur. J. Org. Chem.
2001,
809
14 Flock S.
Skattebol L.
J. Chem. Soc., Perkin Trans. 1
2000,
3071
15 Lévêque L.
Le Blanc M.
Pastor R.
Tetrahedron Lett.
1998,
39:
8857
16 Bose DS.
Narsaiah AV.
Synth. Commun.
1999,
29:
937
17 Yu C.
Hu L.
Tetrahedron Lett.
2001,
42:
5167
18 Jenkins NE.
Ware JRW.
Atkinson RN.
King SB.
Synth. Commun.
2000,
30:
947
19 Roels J.
Metz P.
Synlett
2001,
789
20 Candela Lena JI.
Martin Hernando JI.
Rico Ferreira MdR.
Altinel E.
Arseniyadis S.
Synlett
2001,
597
21 Promarak V.
Burn PL.
J. Chem. Soc., Perkin Trans. 1
2001,
14
22 Nicolaou KC.
Zhong Y.-L.
Baran PS.
Angew. Chem. Int. Ed.
2000,
39:
622
23a Ireland RE.
Liu L.
J. Org. Chem.
1993,
58:
2899
23b Meyer SD.
Schreiber SL.
J. Org. Chem.
1994,
59:
7549
23c Speicher A.
Bomm V.
Eicher T.
J. Prakt. Chem.
1996,
338:
588
24 Viala J.
Sandri J.
Tetrahedron Lett.
1992,
33:
4897
25a Taber DF.
You K.
J. Labelled Compd. Radiopharm.
1994,
34:
747
25b Shing TKM.
Gibson KH.
Wiley JR.
Watt IF.
Tetrahedron Lett.
1994,
35:
1067
26 Durand T.
Guy A.
Vidal J.-P.
Viala J.
Rossi J.-C.
Tetrahedron Lett.
2000,
41:
3859
27a Xu G.
Liu Y.
Sayre LM.
J. Org. Chem.
1999,
64:
5732
27b Xu G.
Sayre LM.
Chem. Res. Toxicol.
1998,
11:
247
27c Yamamoto H.
Maruoka K.
Pure Appl. Chem.
1990,
62:
2063
27d Kobayashi Y.
Shimazaki T.
Taguchi H.
Sato F.
J. Org. Chem.
1990,
55:
5324
28 Viala J.
Santelli M.
Synthesis
1988,
395
