Abstract
Dihydrofuran and dihydropyran epoxides undergo a stereospecific alkylative
double ring-opening with organolithiums to provide a new route to
substituted alkenediols.
Key words
epoxides - organolithiums - alkenes - diols - eliminations
References 1 New address: Xenova Limited, 957 Buckingham
Avenue, Slough, Berks SL1 4NL, UK.
2 Erden I. In
Comprehensive Heterocyclic Chemistry II
Vol. 1A:
Katritzky AR.
Rees CW.
Scriven EFV.
Pergamon Press;
Oxford:
1996.
p.97
3a Crandall JK.
Lin L.-HC.
J. Am. Chem. Soc.
1967,
89:
4526
3b Crandall JK.
Lin L.-HC.
J.
Am. Chem. Soc.
1967,
89:
4527
3c Crandall JK.
Apparu M.
Org. React.
1983,
29:
345
4a Satoh T.
Chem.
Rev.
1996,
96:
3303
4b Doris E.
Dechoux L.
Mioskowski C.
Synlett
1998,
337
5 Dechoux L.
Doris E.
Mioskowski C.
J.
Chem. Soc., Chem. Commun.
1996,
549
6a Hodgson DM.
Lee GP.
Marriott RE.
Thompson AJ.
Wisedale R.
Witherington J.
J. Chem. Soc., Perkin Trans. 1
1998,
2151
6b Hodgson DM.
Robinson LA.
Chem.
Commun.
1999,
309
6c Hodgson DM.
Cameron ID.
Org.
Lett.
2001,
3:
441
6d Hodgson DM.
Cameron ID.
Christlieb M.
Green R.
Lee GP.
Robinson LA.
J.
Chem. Soc., Perkin Trans. 1
2001,
2161
7 Hodgson DM.
Stent MAH.
Wilson FX.
Org. Lett.
2001,
3:
3401
8 5 can be prepared by epoxidation of widely
available 2,5-dihydrofuran: Barili PL.
Berti G.
Mastrorilli E.
Tetrahedron
1993,
49:
6263
9 Calaza MI.
Paleo MR.
Sardina FJ.
J. Am. Chem. Soc.
2001,
123:
2095
10 Dondoni A.
Junquera F.
Merchán FL.
Merino P.
Scherrmann M.-C.
Tejero T.
J. Org.
Chem.
1997,
62:
5484
11 Hudrlik PF.
Peterson D.
J. Am. Chem. Soc.
1975,
97:
1464
12 Fleming I.
Dunoguès J.
Smithers R.
Org.
React.
1989,
37:
57
13 Schulte-Elte KH.
Muller BL.
Pamingle H.
Helv.
Chim. Acta.
1979,
62:
816
14a Bailey WF.
Punzalan ER.
J. Org. Chem.
1990,
55:
5404
14b Negishi E.
Swanson DR.
Rousset CJ.
J. Org. Chem.
1990,
55:
5406
15 Overman LE.
Lesuisse D.
Tetrahedron Lett.
1985,
26:
4167
16a Fu GC.
Nguyen ST.
Grubbs RH.
J. Am. Chem. Soc.
1993,
115:
9856
16b Schwab P.
France MB.
Ziller JW.
Grubbs RH.
Angew.
Chem., Int. Ed. Engl.
1995,
34:
2039
17 Yang D.
Wong M.-K.
Yip Y.-C.
J.
Org. Chem.
1995,
60:
3887
18 Hopkins MH.
Overman LE.
Rishton GM.
J. Am. Chem. Soc.
1991,
113:
5354
19a de Micheli C.
de Amici M.
Grana E.
Zonta F.
Giannella M.
Piergentili A.
Farmaco
1993,
48:
1333
19b Newman MS.
Addor RW.
J.
Am. Chem. Soc.
1955,
77:
3789
20 Epoxidation with m CPBA
(1.1 equiv, CH2 Cl2 , 25 °C, 16 h) gave
epoxides 21 and 22 (21: 22 , 1: 2) in 75% yield.
21a Kasatkin AN.
Whitby RJ.
Tetrahedron Lett.
2000,
41:
5275
21b Boche G.
Lohrenz JCW.
Chem. Rev.
2001,
101:
697
m CPBA, CH2 Cl2 ,
25 °C 16 h) of the corresponding alkenes:
22a Mischitz M.
Kroutil W.
Wandel U.
Faber K.
Tetrahedron: Asymmetry
1995,
6:
1261
22b Hindson AC.
MacCorquodale F.
Walton JC.
J. Chem. Soc., Perkin Trans. 2
1993,
871
22c Reppe W.
Liebigs
Ann. Chem.
1955,
596:
1
22d Malanga C.
Mannucci S.
Lardicci L.
Tetrahedron
1998,
54:
1021
22e Fuji K.
Kawabata T.
Kiryu Y.
Sugiura Y.
Tetrahedron Lett.
1990,
31:
6663
23 Doris E.
Dechoux L.
Mioskowski C.
J.
Am. Chem. Soc.
1995,
117:
12700
24a Suto MJ.
Stier MA.
Werbel LM.
Arundel-Suto CM.
Leopold WR.
Elliott WE.
Sebolt-Leopold JS.
J.
Med. Chem.
1991,
34:
2484
24b Berti G.
Catelani G.
Ferretti M.
Monti L.
Tetrahedron
1974,
30:
4013
25a Chini M.
Crotti P.
Gardelli C.
Macchia F.
Tetrahedron
1994,
50:
1261
25b Booth H.
Khedhair KA.
Readshaw SA.
Tetrahedron
1987,
43:
4699
26 Hodgson DM.
Miles TJ.
Witherington J.
Synlett
2002,
310
27 Falb E.
Nudelman A.
Gottlieb HE.
Hassner A.
Eur. J. Org. Chem.
2000,
645
