Abstract
The Diels-Alder reaction of spirobicyclic cyclopentadiene
derivatives, prepared by reaction of cyclopentadienyllithium and
epichlorohydrin, with maleic anhydride gave a simple access to spiro
tricyclic polyoxygenated compounds of synthetic interest. The solvolytic
behavior of 1-(tosyloxymethyl)spiro[2.4]hepta-4,6-diene,
a 5-spirocyclopentadiene, shows that the ionization of the tosylate
was unlikely.
Key words
tricyclic compounds - Diels-Alder reaction - spiro compounds - stereoselective synthesis
References
1a
Laurenti D.
Feuerstein M.
Pèpe G.
Doucet H.
Santelli M.
J. Org. Chem.
2001,
66:
1633
1b
Doucet H.
Santelli M.
Synlett
2006,
2001
2
Reynaud C.
Fall Y.
Feuerstein M.
Doucet H.
Santelli M.
Tetrahedron
2009,
65:
7440
3a
Bangert K.
Boekelheide V.
Tetrahedron
Lett.
1963,
4:
1119
3b
Corey EJ.
Shiner CS.
Volante RP.
Cyr CR.
Tetrahedron
Lett.
1975,
16:
1161
3c
Lokensgard DM.
Dougherty DA.
Hilinski EF.
Berson JA.
Proc. Natl.
Acad. Sci. U.S.A.
1980,
77:
3090
3d
Attah-Poku SK.
Gallacher G.
Ng AS.
Taylor LEB.
Alward SJ.
Fallis AG.
Tetrahedron Lett.
1983,
24:
677
3e
Gallacher G.
Ng AS.
Attah-Poku SK.
Antczak K.
Alward SJ.
Kingston JF.
Fallis AG.
Can. J. Chem.
1984,
62:
1709
3f
González AG.
Darias J.
Díaz F.
Tetrahedron Lett.
1984,
25:
2697
3g
Antczak K.
Kingston JF.
Fallis AG.
Can. J. Chem.
1985,
63:
993
3h
Antczak K.
Kingston JF.
Fallis A.
Hanson AW.
Can. J. Chem.
1987,
65:
114
3i
Ledford BE.
Carreira EM.
J.
Am. Chem. Soc.
1995,
117:
11811
3j
Starr JT.
Baudat A.
Carreira EM.
Tetrahedron Lett.
1998,
39:
5675
3k
Starr JT.
Koch G.
Carreira EM.
J. Am. Chem. Soc.
2000,
122:
8793
3l
Gorman JST.
Lynch V.
Pagenkopf BL.
Young B.
Tetrahedron
Lett.
2003,
44:
5435
3m
Avilov DV.
Malusare MG.
Arslancan E.
Dittmer DC.
Org.
Lett.
2004,
6:
2225
3n
Nadany AE.
Mckendrick JE.
Tetrahedron
Lett.
2007,
48:
4071
4 For example, for syn -isomers 2a and 2c , the
chemical shifts of carbon atoms of anhydrides are different, and
for anti -isomers 3a and 3c the chemical shifts are identical.
5
Frisch MJ.
Trucks GW.
Schlegel HB.
Scuseria GE.
Robb MA.
Cheeseman JR.
Montgomery JA.
Vreven T.
Kudin KN.
Burant JC.
Millam JM.
Iyengar SS.
Tomasi J.
Barone V.
Mennucci B.
Cossi M.
Scalmani G.
Rega N.
Petersson GA.
Nakatsuji H.
Hada M.
Ehara M.
Toyota K.
Fukuda R.
Hasegawa J.
Ishida M.
Nakajima T.
Honda Y.
Kitao O.
Nakai H.
Klene M.
Li X.
Knox JE.
Hratchian HP.
Cross JB.
Bakken V.
Adamo C.
Jaramillo J.
Gomperts R.
Stratmann RE.
Yazyev O.
Austin AJ.
Cammi R.
Pomelli C.
Ochterski JW.
Ayala PY.
Morokuma K.
Voth GA.
Salvador P.
Dannenberg JJ.
Zakrzewski VG.
Dapprich S.
Daniels AD.
Strain MC.
Farkas O.
Malick DK.
Rabuck AD.
Raghavachari K.
Foresman JB.
Ortiz JV.
Cui Q.
Baboul AG.
Clifford S.
Cioslowski J.
Stefanov BB.
Liu G.
Liashenko A.
Piskorz P.
Komaromi I.
Martin RL.
Fox DJ.
Keith T.
Al-Laham MA.
Peng CY.
Nanayakkara A.
Challacombe M.
Gill PMW.
Johnson B.
Chen W.
Wong MW.
Gonzalez C.
Pople JA.
Gaussian 03, Revision E.01
Gaussian
Inc.;
Wallingford (CT):
2004.
6
Saunders J.
Tipney DC.
Robins P.
Tetrahedron
Lett.
1982,
23:
4147
7a
Coxon JM.
McDonald DQ.
Tetrahedron Lett.
1992,
33:
651
7b
Werstiuk NH.
Ma J.
Macaulay JB.
Fallis AG.
Can.
J. Chem.
1992,
70:
2798
7c For recent studies and
references, see: Ishida M.
Itakura M.
Tashiro H.
Tetrahedron
Lett.
2008,
49:
1804
8 Special Issue: Nonclassical Carbocations, Acc. Chem. Res.
1983 , 16, 425
9
Oda M.
Breslow R.
Tetrahedron Lett.
1973,
14:
2537
10
Warrener RN.
Harrison PA.
Sterns M.
Russell RA.
J. Chem. Soc., Chem.
Commun.
1984,
546
11a
Kornblum N.
Jones WJ.
Anderson GJ.
J. Am. Chem. Soc.
1959,
81:
4113
11b
Smith MB.
March J.
March’s Advanced Organic Chemistry
6th
ed.:
Wiley;
Hoboken (NJ):
2007.
p.1765
12 The silver-assisted solvolysis of
cyclopentadien-5-yl iodide is at least 105 times slower
than that of cyclopentyl iodide, see: Breslow R.
Hoffman JM.
J. Am.
Chem. Soc.
1972,
94:
2110
13
de Vries EFJ.
Brussee J.
van
der Gen A.
J. Org. Chem.
1994,
59:
7133
14 X-ray crystallography: CCDC-794286
(for 3b ), contain the supplementary crystallographic
data for this paper. These data can be obtained free of charge at
www.ccdc.cam.ac.uk/conts/retrieving.html [or
from the Cambridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 (1223)336033; or e-mail: deposit@ccdc.cam.ac.uk].