Abstract
The formal [3+3] cyclization of 1,3-bis(siloxy)buta-1,3-dienes
with 2-(arylsulfonyl)-3-ethoxy-2-en-1-ones, readily available by
reaction of β-keto sulfones with triethyl orthoformate,
allows the synthesis of a variety of functionalized diaryl sulfones
with very good regioselectivity.
Key words
arenes - sulfones - cyclizations - regioselectivity - silyl enol ethers
References
<A NAME="RT01109SS-1A">1a </A>
Shrimali SS.
Joshi BC.
Kishore D.
J. Indian
Chem. Soc.
1988,
65:
438
<A NAME="RT01109SS-1B">1b </A>
Upadhyay PS.
Vansdadia RN.
Baxi AJ.
Indian J. Chem., Sect. B: Org. Chem.
Incl. Med. Chem.
1990,
29:
793
<A NAME="RT01109SS-2">2 </A>
Teshirogi I.
Matsutani S.
Shirahase K.
Fujii Y.
Yoshida T.
J.
Med. Chem.
1996,
39:
5183
<A NAME="RT01109SS-3">3 </A>
Paulini R.
Lerner C.
Diederich F.
Jakob-Roetne R.
Zuercher G.
Borroni E.
Helv. Chim. Acta
2006,
89:
1856
<A NAME="RT01109SS-4A">4a </A>
de Benedetti PG.
Iarossi D.
Menziani C.
Caiolfa V.
Frassineti C.
Cennamo C.
J.
Med. Chem.
1987,
30:
459
<A NAME="RT01109SS-4B">4b </A>
de Benedetti PG.
Iarossi D.
Folli U.
Frassineti C.
Menziani MC.
Cennamo C.
J.
Med. Chem.
1989,
32:
2396
<A NAME="RT01109SS-5">5 </A>
Sircar I.
Hoefle M.
Maxwell RE.
J.
Med. Chem.
1983,
26:
1020
<A NAME="RT01109SS-6">6 </A>
Markley LD.
Tong YC.
Dulworth JK.
Steward DL.
Goralski CT.
J. Med. Chem.
1986,
29:
427
<A NAME="RT01109SS-7">7 </A>
Wright J.
Bolton G.
Creswell M.
Downing D.
Georgic L.
Bioorg.
Med. Chem. Lett.
1996,
6:
1809
<A NAME="RT01109SS-8A">8a </A>
Neamati N.
Mazumder A.
Zhao H.
Sunder S.
Burke TR.
Schultz RJ.
Pommier Y.
Antimicrob. Agents Chemother.
1997,
41:
385
<A NAME="RT01109SS-8B">8b </A>
Chan JH.
Hong JS.
Hunter RN.
Orr GF.
Cowan JR.
Sherman DB.
Sparks SM.
Reitter BE.
Andrews CW.
Hazen RJ.
Clair MS.
J.
Med. Chem.
2001,
44:
1866
<A NAME="RT01109SS-8C">8c </A>
Tagat JR.
McCombie SW.
Steensma RW.
Lin S.-I.
Nazareno
DV.
Baroudy B.
Vantuno N.
Xu S.
Liu J.
Bioorg. Med. Chem. Lett.
2001,
11:
2143
<A NAME="RT01109SS-9">9 </A>
Stanton JL.
Cahill E.
Dotson R.
Tan J.
Tomaselli
HC.
Wasvary JM.
Stephan ZF.
Steele RE.
Bioorg. Med.
Chem. Lett.
2000,
10:
1661
<A NAME="RT01109SS-10A">10a </A>
Kozlowski JA.
Zhou G.
Tagat JR.
Lin S.-I.
McCombie SW.
Ruperto VB.
Duffy RA.
McQuade RA.
Crosby G.
Taylor LA.
Billard W.
Bioorg.
Med. Chem. Lett.
2002,
12:
791
<A NAME="RT01109SS-10B">10b </A>
Wang Y.
Chackalamannil S.
Hu Z.
Clader JW.
Greenlee W.
Billard W.
Binch H.
Crosby G.
Ruperto V.
Duffy RA.
McQuade R.
Lachowicz JE.
Bioorg. Med. Chem.
Lett.
2000,
10:
2247
<A NAME="RT01109SS-10C">10c </A>
Boyle CD.
Chackalamannil S.
Chen L.-Y.
Dugar S.
Pushpavanam P.
Billard W.
Binch H.
Crosby G.
Cohen-Williams M.
Coffin VL.
Duffy RA.
Bioorg. Med. Chem. Lett.
2000,
10:
2727
<A NAME="RT01109SS-10D">10d </A>
Wang Y.
Chackalamannil S.
Chang W.
Greenlee W.
Ruperto V.
Duffy RA.
McQuade R.
Lachowicz JE.
Bioorg. Med. Chem.
Lett.
2001,
11:
891
<A NAME="RT01109SS-10E">10e </A>
Boyle CD.
Chackalamannil S.
Clader JW.
Greenlee WJ.
Josien HB.
Kaminski JJ.
Kozlowski JA.
McCombie SW.
Nazareno DV.
Tagat JR.
Wang Y.
Bioorg.
Med. Chem. Lett.
2001,
11:
2311
<A NAME="RT01109SS-10F">10f </A>
Boyle CD.
Vice SF.
Campion J.
Chackalamannil S.
Lankin CM.
McCombie SW.
Billard W.
Binch H.
Crosby G.
Williams M.-C.
Coffin VL.
Bioorg. Med. Chem.
Lett.
2002,
12:
3479
<A NAME="RT01109SS-11">11 </A>
Sasse A.
Ligneau X.
Sadek B.
Elz S.
Pertz HH.
Ganellin CR.
Arrang J.-M.
Schwartz J.-C.
Schunack W.
Stark H.
Arch. Pharm. (Weinheim, Ger.)
2001,
334:
45
<A NAME="RT01109SS-12">12 </A>
Langler RF.
Paddock RL.
Thompson DB.
Crandall I.
Ciach M.
Kain KC.
Aust.
J. Chem.
2003,
56:
1127
<A NAME="RT01109SS-13">13 </A>
Clark RD.
Jahangir A.
Severance D.
Salazar R.
Chang T.
Chang D.
Jett MF.
Smith S.
Bley K.
Bioorg. Med.
Chem. Lett.
2004,
14:
1053
<A NAME="RT01109SS-14">14 </A>
Lavey BJ.
Kozlowski JA.
Hipkin RW.
G onsiorek W.
Lundell DJ.
Piwinski JJ.
Narula S.
Lunn CA.
Bioorg.
Med. Chem. Lett.
2005,
15:
783
<A NAME="RT01109SS-15">15 </A>
Lu I.-L.
Mahindroo N.
Liang P.-H.
Peng Y.-H.
Kuo C.-J.
Tsai K.-C.
Hsieh H.-P.
Chao Y.-S.
Wu S.-Y.
J. Med.
Chem.
2006,
9:
5154
<A NAME="RT01109SS-16">16 </A>
Joseph JK.
Jain SL.
Sain B.
Synth.
Commun.
2006,
36:
2743
<A NAME="RT01109SS-17A">17a </A>
Chen D.-W.
Kubiak RJ.
Ashley JA.
Janda KD.
J. Chem. Soc., Perkin Trans. 1
2001,
21:
2796
<A NAME="RT01109SS-17B">17b </A>
Marquie J.
Laporterie A.
Dubac J.
Roques N.
Desmurs J.-R.
J. Org.
Chem.
2001,
66:
421
<A NAME="RT01109SS-17C">17c </A>
Repichet S.
Le Roux C.
Dubac J.
Tetrahedron
Lett.
1999,
40:
9233
<A NAME="RT01109SS-17D">17d </A>
Hajipour AR.
Zarei A.
Khazdooz L.
Pourmousavi SA.
Mirjalili BBF.
Ruoho AE.
Phosphorus, Sulfur Silicon Relat.
Elem.
2005,
180:
2029
<A NAME="RT01109SS-18">18 </A>
Woroshzow V.
Kutschkarow V.
Zh. Obshch. Khim.
1949,
19:
1943 ; Chem. Abstr. 1950 , 1922
<A NAME="RT01109SS-19">19 </A>
Zhu W.
Ma D.
J. Org. Chem.
2005,
70:
2696
<A NAME="RT01109SS-20">20 </A>
Bandgar BP.
Bettigeri SV.
Phopase J.
Org.
Lett.
2004,
6:
2105
<A NAME="RT01109SS-21">21 </A>
Huang F.
Batey RA.
Tetrahedron
2007,
63:
7667
<A NAME="RT01109SS-22">22 </A>
Erian AW.
Issac Y.
Sherif SM.
Mahmoud FF.
J. Chem.
Soc., Perkin Trans. 1
2000,
3686
<A NAME="RT01109SS-23A">23a </A>
Ogura K.
Takeda M.
Xie JR.
Akazome M.
Matsumoto S.
Tetrahedron Lett.
2001,
42:
1923
<A NAME="RT01109SS-23B">23b </A>
Matsumoto S.
Kumazawa K.
Ogura K.
Bull.
Chem. Soc. Jpn.
2003,
76:
2179
<A NAME="RT01109SS-23C">23c </A>
Bianchi L.
Dell’Erba C.
Maccagno M.
Mugnoli A.
Novi M.
Petrillo G.
Sancassan F.
Tavani C.
J. Org. Chem.
2003,
68:
5254
<A NAME="RT01109SS-24">24 </A>
Mutsuhiro Y.
Watanabe M.
Furukawa S.
Chem.
Pharm. Bull.
1990,
38:
902
<A NAME="RT01109SS-25">25 </A>
Padwa A.
Gareau Y.
Harrison B.
Rodriguez A.
J. Org. Chem.
1992,
57:
3540
<A NAME="RT01109SS-26">26 </A>
Hayakawa K.
Nishiyama H.
Kanematsu K.
J.
Org. Chem.
1985,
50:
512
<A NAME="RT01109SS-27">27 </A>
Nakayama J.
Hirashima A.
J. Am. Chem. Soc.
1990,
112:
7648
<A NAME="RT01109SS-28">28 </A>
Hu C.-M.
Hong F.
Jiang B.
Xu Y.
J. Fluorine Chem.
1994,
66:
215
<A NAME="RT01109SS-29">29 </A>
Antelo B.
Castedo L.
Delamano J.
Gomes A.
Lopez C.
Tojo G.
J. Org. Chem.
1996,
61:
1188
<A NAME="RT01109SS-30">30 </A>
Bull JR.
Desmond-Smith NS.
Heggie SJ.
Hunter R.
Tien F.-C.
Synlett
1998,
900
<A NAME="RT01109SS-31">31 </A>
Chan T.-H.
Brownbridge P.
J. Am. Chem. Soc.
1980,
102:
3534
<A NAME="RT01109SS-32">32 </A> For a review of [3+3] cyclizations
of 1,3-bis(silyl enol ethers), see:
Feist H.
Langer P.
Synthesis
2007,
327
<A NAME="RT01109SS-33">33 </A> For a review of the chemistry of
1,3-bis(silyl enol ethers), see:
Langer P.
Synthesis
2002,
441
<A NAME="RT01109SS-34">34 </A>
Riahi A.
Shkoor M.
Fatunsin O.
Lubbe M.
Reinke H.
Langer P.
Tetrahedron Lett.
2009,
50:
115
<A NAME="RT01109SS-35">35 </A>
Molander GA.
Cameron KO.
J. Am. Chem. Soc.
1993,
115:
830
<A NAME="RT01109SS-36">36 </A>
Nguyen VTH.
Bellur E.
Appel B.
Synthesis
2006,
2865
<A NAME="RT01109SS-37A">37a </A>
Reiter LA.
J. Org. Chem.
1984,
49:
3494
<A NAME="RT01109SS-37B">37b </A>
Lemcke T.
Messinger P.
Arch. Pharm. (Weinheim, Ger.)
1995,
328:
269
<A NAME="RT01109SS-38A">38a </A>
Brownbridge P.
Chan TH.
Brook MA.
Kang GJ.
Can.
J. Chem.
1983,
61:
688
<A NAME="RT01109SS-38B">38b </A>
Hirai K.
Ojima I.
Tetrahedron Lett.
1983,
24:
785
<A NAME="RT01109SS-39">39 </A>
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