Abstract
The relevance of four-membered-ring substructures in organic
synthesis is undeniable, and well reflected by the breadth of synthetic
approaches to cyclobutanes reported in the literature. As comparatively
more versatile synthetic intermediates, cyclobutenes have been the
object of fewer studies. This account briefly reviews those prior
reports and highlights a recent breakthrough in the stereoselective,
atom-economical, and direct preparation of cyclobutenes
through an intriguing combination of photochemistry and metal catalysis.
Key words
cyclobutenes - palladium - stereoselective
synthesis - rearrangement - atom economy
References and Notes
<A NAME="RP00510ST-1">1</A>
Carbocyclic Four-Membered
Ring Compounds, In Methods of Organic Chemistry (Houben-Weyl)
Vol.
17e:
de Meijere A.
Thieme;
Stuttgart:
1997.
<A NAME="RP00510ST-2">2</A>
Organic Synthesis: Theory
and Applications
Vol. 5:
Hansen TV.
Stenstrøm Y.
Elsevier;
Amsterdam:
1996.
p.1-38.
<A NAME="RP00510ST-3A">3a</A>
Lee-Ruff E.
Mladenova G.
Chem.
Rev.
2003,
103:
1449
<A NAME="RP00510ST-3B">3b</A>
Namyslo JC.
Kaufmann DE.
Chem.
Rev.
2003,
103:
1485
<A NAME="RP00510ST-4">4</A>
Carbocyclic Four-Membered
Ring Compounds, In Methods of Organic Chemistry (Houben-Weyl)
Vol.
17f:
de Meijere A.
Thieme;
Stuttgart:
1997.
<A NAME="RP00510ST-5A">5a</A>
Salaün J.
Fadel A.
Org.
Synth.
1986,
64:
50
<A NAME="RP00510ST-5B">5b</A>
Semmelhack MF.
Tomoda S.
J. Am. Chem.
Soc.
1981,
103:
2427
<A NAME="RP00510ST-6A">6a</A>
Commandeur M.
Commandeur C.
De Paolis M.
Edmunds AJF.
Maienfisch P.
Ghosez L.
Tetrahedron Lett.
2009,
50:
3359
<A NAME="RP00510ST-6B">6b</A>
Takasu K.
Synlett
2009,
1905
<A NAME="RP00510ST-7">7</A>
Gauvry N.
Lescop C.
Huet F.
Eur.
J. Org. Chem.
2006,
5207
<A NAME="RP00510ST-8A">8a</A>
Sampath V.
Lund EC.
Knudsen MJ.
Olmstead
MM.
Schore NE.
J.
Org. Chem.
1987,
52:
3595
<A NAME="RP00510ST-8B">8b</A>
Gauvry N.
Comoy C.
Lescope C.
Huet F.
Synthesis
1999,
574
<A NAME="RP00510ST-9A">9a</A>
Jung ME.
Sledeski AW.
J. Chem. Soc., Chem. Commun.
1993,
589
<A NAME="RP00510ST-9B">9b</A>
Binns F.
Hayes R.
Hodgetts
KJ.
Saengchantara ST.
Wallace TW.
Wallis CJ.
Tetrahedron
1996,
52:
3631
<A NAME="RP00510ST-9C">9c</A>
Gourdel-Martin M.-E.
Comoy C.
Huet F.
Tetrahedron: Asymmetry
1999,
10:
403
<A NAME="RP00510ST-9D">9d</A>
Baldwin JE.
Burrell RC.
J.
Org. Chem.
2000,
65:
7139
<A NAME="RP00510ST-9E">9e</A>
Ogawa S.
Urabe D.
Yokokura Y.
Arai H.
Arita M.
Inoue M.
Org. Lett.
2009,
11:
3602
<A NAME="RP00510ST-10A">10a</A>
Alibés R.
de March P.
Figueredo M.
Font J.
Racamonde M.
Rustullet A.
Alvarez-Larena A.
Piniella JF.
Parella T.
Tetrahedron
Lett.
2003,
44:
69
<A NAME="RP00510ST-10B">10b</A>
Alibés R.
de March P.
Figueredo M.
Font J.
Racamonde M.
Parella T.
Org. Lett.
2004,
6:
1449
<A NAME="RP00510ST-11A">11a</A>
Shi M.
Liu LP.
Tang J.
J. Am Chem. Soc.
2006,
128:
7430
<A NAME="RP00510ST-11B">11b</A>
Lopez-Carrillo V.
Echavarren AM.
J.
Am Chem. Soc.
2010,
132:
9292
<A NAME="RP00510ST-11C">11c</A>
Fürstner A.
Davies PW.
Gress T.
J. Am Chem. Soc.
2005,
127:
8244
<A NAME="RP00510ST-11D">11d</A>
Trost BM.
Gutierrez AC.
Ferreira EM.
J. Am. Chem. Soc.
2010,
132:
9206
For a more complete list of references about transition-metal-catalysed
approaches to cyclobutenes, see:
<A NAME="RP00510ST-11E">11e</A>
Lee YT.
Kang YK.
Chung YK.
J. Org. Chem.
2009,
74:
7922 ; and references cited therein
<A NAME="RP00510ST-11F">11f</A>
Odabachian Y.
Gagosz F.
Adv. Synth Catal.
2009,
351:
379 ; and references cited therein
<A NAME="RP00510ST-12A">12a</A>
Debleds O.
Campagne JM.
J.
Am Chem. Soc.
2008,
130:
1562
<A NAME="RP00510ST-12B">12b</A>
Graham TJA.
Gray EE.
Burgess JM.
Goess BC.
J. Org. Chem.
2010,
75:
226
For a few notable exceptions, see:
<A NAME="RP00510ST-13A">13a</A>
Liu Y.
Liu M.
Song Z.
J.
Am. Chem. Soc.
2005,
127:
3662
<A NAME="RP00510ST-13B">13b</A>
Xu H.
Zhang W.
Shu D.
Werness JB.
Tang W.
Angew.
Chem. Int. Ed.
2008,
47:
8933
<A NAME="RP00510ST-13C">13c</A>
Takachi M.
Kita Y.
Tobisu M.
Fukumoto Y.
Chatani N.
Angew. Chem.
Int. Ed.
2010,
49:
8717
<A NAME="RP00510ST-13D">13d</A>
Xia JB.
Liu WB.
Wang TM.
You SL.
Chem.
Eur. J.
2010,
16:
6442
<A NAME="RP00510ST-14">14</A>
Frébault F.
Luparia M.
Oliveira MT.
Goddard R.
Maulide N.
Angew.
Chem. Int. Ed.
2010,
49:
5672
<A NAME="RP00510ST-15">15</A>
Corey EJ.
Streith J.
J. Am. Chem. Soc.
1964,
86:
950
For further studies on the photochemical
conversion of 1 into 2,
see:
<A NAME="RP00510ST-16A">16a</A>
Javaheripour H.
Neckers DC.
J. Org. Chem.
1977,
42:
1844
<A NAME="RP00510ST-16B">16b</A>
Pirkle WH.
McKendry LH.
J.
Am. Chem. Soc.
1969,
91:
1179
<A NAME="RP00510ST-16C">16c</A>
Arnold BR.
Brown CE.
Lusztyk J.
J. Am. Chem. Soc.
1993,
115:
1576
<A NAME="RP00510ST-16D">16d</A>
Breda S.
Reva I.
Lapinski L.
Fausto R.
Phys. Chem. Chem. Phys.
2004,
6:
929
To our knowledge, only one report on the ring opening of 2 (by the use of concentrated HCl) has appeared
in the literature; see ref. 15a. For use of lactones akin to 2 in the preparation of cyclobutadienes,
see:
<A NAME="RP00510ST-16E">16e</A>
Legrand Y.-M.
van der Lee A.
Barboiu M.
Science
2010,
329:
299
<A NAME="RP00510ST-17A">17a</A>
Tsuji J. In Palladium Reagents and Catalysts
Wiley;
New
York:
1996.
Chap. 4.
p.290-404
<A NAME="RP00510ST-17B">17b</A>
Frost CG.
Howarth J.
Williams JMJ.
Tetrahedron: Asymmetry
1992,
3:
1089
<A NAME="RP00510ST-17C">17c</A>
Hayashi T.
In
Catalytic Asymmetric Synthesis
Ojima I.
VCH
Publishers;
New York:
1993.
p.325
<A NAME="RP00510ST-17D">17d</A>
Trost BM.
Van Vranken DL.
Chem.
Rev.
1996,
96:
395
<A NAME="RP00510ST-18">18</A>
For ease of purification, most of
the crude acids 3 were routinely converted
into the corresponding methyl esters.
For the use of α,α-disubstituted
(quaternary) α-amino acids in peptidomimetics, see:
<A NAME="RP00510ST-19A">19a</A>
Trost BM.
Ariza X.
J. Am. Chem.
Soc.
1999,
121:
10727 ;
and references cited therein
For reviews on α,α-disubstituted (quaternary) α-amino acids,
see:
<A NAME="RP00510ST-19B">19b</A>
Cativiela C.
Diaz-de-Villegas MD.
Tetrahedron:
Asymmetry
1998,
9:
3517
<A NAME="RP00510ST-19C">19c</A>
Cativiela C.
Diaz-de-Villegas MD.
Tetrahedron:
Asymmetry
2000,
11:
645
<A NAME="RP00510ST-19D">19d</A>
Ohfune Y.
Shinada T.
Eur. J. Org. Chem.
2005,
5127
<A NAME="RP00510ST-19E">19e</A>
Vogt H.
Bräse S.
Org. Biomol. Chem.
2007,
5:
406
<A NAME="RP00510ST-20">20</A>
The structure was confirmed by single-crystal
X-ray analysis.
<A NAME="RP00510ST-21">21</A>
Pulici M.
Sugawara F.
Koshino H.
Uzawa J.
Yoshida S.
Lobkovsky E.
Clardy J.
J.
Org. Chem.
1996,
61:
2122
<A NAME="RP00510ST-22">22</A>
Pandey G.
Banerjee P.
Gadre SR.
Chem.
Rev.
2006,
106:
4484
<A NAME="RP00510ST-23A">23a</A>
Masarwa A.
Fürstner A.
Marek I.
Chem. Commun.
2009,
5760 ; and references cited therein
<A NAME="RP00510ST-23B">23b</A>
Darses B.
Greene AE.
Poisson J.-F.
Org.
Lett.
2010,
12:
3994
