Abstract
Cycloaddition and cycloisomerization based on the interaction
between an allene and another multiple bond, such as an alkyne,
alkene, or additional allene, enabled us to build a variety of useful
cyclic structures. This account describes our research on allene
cycloaddition and cycloisomerization, categorizing the reactions
by the proper reaction mode and the cyclic framework of the product.
1 Introduction
2 Construction of Bicyclo[m.3.0] Skeletons
via Carbonylative [2+2+1] Cycloaddition
2.1 From Allene-Ynes and Aza Analogues
2.2 From Allene-Enes
2.3 From Bis-allenes
3 Construction of Bicyclo[m.2.0] Skeletons
via [2+2] Cycloaddition
3.1 From Allene-Ynes
3.2 From Bis-allenes
4 Construction of Bicyclo[4.4.0] Skeletons
via 6π-Electrocyclization/[4+2] Cycloaddition
5 Construction of Monocyclic Polyenes via Cycloisomerization
5.1 From Allene-Ynes
5.2 From Allene-Enes
5.3 From Bis-allenes
6 Construction of Bicyclo[5.m.0] Skeletons
via [5+2] Cycloaddition
7 Conclusions and Outlook
Key words
allenes - cycloadditions - Pauson-Khand-type
reactions - cycloisomerizations - medium-sized rings
References
1a
Landor SR.
The
Chemistry of the Allenes
Academic;
London:
1982.
1b
Schuster HF.
Coppola GM.
Allenes in Organic Synthesis
Wiley;
New
York:
1984.
1c
Pasto DJ.
Tetrahedron
1984,
40:
2805
1d
Zimmer R.
Dinesh CU.
Nandanan E.
Khan FA.
Chem. Rev.
2000,
100:
3067
1e
Hashmi ASK.
Angew. Chem. Int. Ed.
2000,
39:
3590
1f
Hoffmann-Röder A.
Krause N.
Angew. Chem.
Int. Ed.
2004,
43:
1196
1g
Krause N.
Hashmi ASK.
Modern Allene Chemistry
Wiley-VCH;
Weinheim:
2004.
1h
Ma S.
Chem.
Rev.
2005,
105:
2829
1i
Brummond KM.
DeForrest JE.
Synthesis
2007,
795
2a
Khand IU.
Knox GR.
Pauson PL.
Watts WE.
J. Chem. Soc. D
1971,
36a
2b
Khand IU.
Knox GR.
Pauson PL.
Watts WE.
Foreman MI.
J. Chem. Soc., Perkin
Trans. 1
1973,
977
For selected reviews, see:
3a
Geis O.
Schmalz H.-G.
Angew. Chem. Int. Ed.
1998,
37:
911
3b
Brummond KM.
Kent JL.
Tetrahedron
2000,
56:
3263
3c
Gibson
SE.
Stevenazzi A.
Angew.
Chem. Int. Ed.
2003,
42:
1800
3d
Blanco-Urgoiti J.
Añorbe L.
Pérez-Serrano L.
Domínguez G.
Pérez-Castells J.
Chem. Soc. Rev.
2004,
33:
32
3e
Boñaga LVR.
Krafft ME.
Tetrahedron
2004,
60:
9795
3f
Shibata T.
Adv.
Synth. Catal.
2006,
348:
2328
For the construction of seven-membered
and larger rings via the Pauson-Khand reaction of enynes with aromatic
rings as a template, see:
4a
Pérez-Serrano L.
Casarrubios L.
Domínguez G.
Pérez-Castells J.
Chem.
Commun.
2001,
2602
4b
Krafft ME.
Fu Z.
Boñaga LVR.
Tetrahedron Lett.
2001,
42:
1427
4c
Lovely CJ.
Seshadri H.
Wayland BR.
Cordes AW.
Org.
Lett.
2001,
3:
2607
5a
Mukai C.
Uchiyama M.
Sakamoto S.
Hanaoka M.
Tetrahedron
Lett.
1995,
36:
5761
5b
Mukai C.
Kim JS.
Uchiyama M.
Sakamoto S.
Hanaoka M.
J.
Chem. Soc., Perkin Trans. 1
1998,
2903
5c
Mukai C.
Kim JS.
Uchiyama M.
Hanaoka M.
Tetrahedron Lett.
1998,
39:
7909
5d
Mukai C.
Kim JS.
Sonobe H.
Hanaoka M.
J. Org. Chem.
1999,
64:
6822
5e
Mukai C.
Sonobe H.
Kim JS.
Hanaoka M.
J. Org. Chem.
2000,
65:
6654
Intramolecular allenic [2+2+1] cycloaddition
was first reported by Narasaka and Brummond and their co-workers, see:
6a
Narasaka K.
Shibata T.
Chem. Lett.
1994,
315
6b
Shibata T.
Koga Y.
Narasaka K.
Bull.
Chem. Soc. Jpn.
1995,
68:
911
6c
Kent JL.
Wan H.
Brummond KM.
Tetrahedron Lett.
1995,
36:
2407
6d
Brummond KM.
Wan H.
Kent JL.
J. Org. Chem.
1998,
63:
6535
For reviews of allenic [2+2+1] cycloadditions,
see:
7a
Brummond KM.
An Allenic [2+2+1] Cycloaddition, In Advances in Cycloaddition
Vol.
6:
Harmata M.
JAI;
Stamford:
1999.
p.211-237
7b
Alcaide B.
Almendros P.
Eur. J. Org. Chem.
2004,
3377
8
Ahmar M.
Locatelli C.
Colombier D.
Cazes B.
Tetrahedron Lett.
1997,
38:
5281
9a
Mukai C.
Yamashita H.
Hanaoka M.
Org. Lett.
2001,
3:
3385
9b
Mukai C.
Ohta M.
Yamashita H.
Kitagaki S.
J. Org. Chem.
2004,
69:
6867
10
Kitagaki S.
Inagaki F.
Mukai C.
J.
Synth. Org. Chem., Jpn.
2009,
67:
618
11
Horner L.
Binder V.
Justus Liebigs Ann. Chem.
1972,
757:
33
12a
Nájera C.
Yus M.
Tetrahedron
1999,
55:
10547
12b
Simpkins NS.
Sulphones in Organic
Synthesis
Pergamon;
Oxford:
1993.
13a
Mukai C.
Nomura I.
Yamanishi K.
Hanaoka M.
Org. Lett.
2002,
4:
1755
13b
Mukai C.
Nomura I.
Kitagaki S.
J.
Org. Chem.
2003,
68:
1376
Rhodium(I)-catalyzed carbonylative [2+2+1] cycloaddition was
first reported by Narasaka and co-workers and Jeong et al., see:
14a
Koga Y.
Kobayashi T.
Narasaka K.
Chem. Lett.
1998,
249
14b
Kobayashi T.
Koga Y.
Narasaka K.
J.
Organomet. Chem.
2001,
624:
73
14c
Jeong N.
Lee S.
Sung BK.
Organometallics
1998,
17:
3642
15
Sanger AR.
J.
Chem. Soc., Dalton Trans.
1977,
120
16 Brummond et al. independently developed
the [RhCl(CO)2]2-catalyzed [2+2+1] cycloaddition
of allene-ynes, see: Brummond KM.
Chen H.
Fisher KD.
Kerekes AD.
Rickards B.
Sill PC.
Geib SJ.
Org.
Lett.
2002,
4:
1931
17
Mukai C.
Inagaki F.
Yoshida T.
Yoshitani K.
Hara Y.
Kitagaki S.
J. Org. Chem.
2005,
70:
7159
18
Mukai C.
Hirose T.
Teramoto S.
Kitagaki S.
Tetrahedron
2005,
61:
10983
19
Inagaki F.
Kawamura T.
Mukai C.
Tetrahedron
2007,
63:
5154
20
Bayden AS.
Brummond KM.
Jorden KD.
Organometallics
2006,
25:
5204
21
Mukai C.
Inagaki F.
Yoshida T.
Kitagaki S.
Tetrahedron Lett.
2004,
45:
4117
22
Hirose T.
Miyakoshi N.
Mukai C.
J.
Org. Chem.
2008,
73:
1061
23
Aburano D.
Inagaki F.
Tomonaga S.
Mukai C.
J. Org. Chem.
2009,
74:
5590
24
Saito T.
Shiotani M.
Otani T.
Hasaba S.
Heterocycles
2003,
60:
1045
25
Tang Y.
Deng L.
Zhang Y.
Dong G.
Chen J.
Yang Z.
Org.
Lett.
2005,
7:
593
26a
Mukai C.
Yoshida T.
Sorimachi M.
Odani A.
Org. Lett.
2006,
8:
83
26b
Aburano D.
Yoshida T.
Miyakoshi N.
Mukai C.
J. Org. Chem.
2007,
72:
6878
27
Saito T.
Sugizaki K.
Otani T.
Suyama T.
Org. Lett.
2007,
9:
1239
28
Negishi E.
Choueiry D.
Nguyen TB.
Swanson DR.
Suzuki N.
Takahashi T.
J. Am. Chem. Soc.
1994,
116:
9751
29a
Wender PA.
Croatt MP.
Deschamps NM.
J.
Am. Chem. Soc.
2004,
126:
5948
29b In this paper, Wender
et al. reported that several dienes failed to give the [2+2+1] cycloadducts
under the optimized [RhCl(CO)2]2-catalyzed conditions.
30
Makino T.
Itoh K.
J. Org. Chem.
2004,
69:
395
31
Inagaki F.
Mukai C.
Org. Lett.
2006,
8:
1217
32a
Bolton GL.
Hodges JC.
Rubin JR.
Tetrahedron
1997,
53:
6611
32b
Ishizaki M.
Satoh H.
Hoshino O.
Chem.
Lett.
2002,
1040
32c
Ishizaki M.
Sato H.
Hoshino O.
Nishitani K.
Hara H.
Heterocycles
2004,
63:
827
33
Hayashi Y.
Miyakoshi N.
Kitagaki S.
Mukai C.
Org. Lett.
2008,
10:
2385
34a
Inagaki F.
Narita S.
Hasegawa T.
Kitagaki S.
Mukai C.
Angew. Chem. Int. Ed.
2009,
48:
2007
34b
Kawamura T.
Inagaki F.
Narita S.
Takahashi Y.
Hirata S.
Kitagaki S.
Mukai C.
Chem.
Eur. J.
2010,
16:
5173
35 Chung and co-workers reported the
cobalt/rhodium-nanoparticle-catalyzed [2+2+1] cycloaddition
of 1,5-bis-allenes, see: Park JH.
Kim E.
Kim H.-M.
Choi SY.
Chung YK.
Chem.
Commun.
2008,
2388
36 Recently, Ma and co-workers reported
the rhodium-catalyzed and molybdenum-mediated [2+2+1] cycloaddition
of 1,5-bis-allenes in a review article, see: Chen G.
Jiang X.
Fu C.
Ma S.
Chem. Lett.
2010,
39:
78
37
Watanabe Y.
Ueno Y.
Araki T.
Endo T.
Okawara M.
Tetrahedron
Lett.
1986,
27:
215
For other examples dealing with
the desulfonylation of our products, see:
38a
Miyakoshi N.
Ohgaki Y.
Masui K.
Mukai C.
Heterocycles
2007,
74:
185
38b See also ref. 23
39
Brummond KM.
Chen D.
Org. Lett.
2005,
7:
3473
40
Oh CH.
Gupta AK.
Park DI.
Kim N.
Chem. Commun.
2005,
5670
41
Mukai C.
Hara Y.
Miyashita Y.
Inagaki F.
J. Org. Chem.
2007,
72:
4454
42a
Padwa A.
Filipkowski MA.
Meske M.
Watterson
SH.
Ni Z.
J. Am. Chem.
Soc.
1993,
115:
3776
42b
Padwa A.
Meske M.
Murphree SS.
Watterson SH.
Ni Z.
J.
Am. Chem. Soc.
1995,
117:
7071
42c
Padwa A.
Lipka H.
Watterson SH.
Murphree SS.
J. Org. Chem.
2003,
68:
6238
43
Siebert MR.
Osbourn JM.
Brummond KM.
Tantillo DJ.
J.
Am. Chem. Soc.
2010,
132:
11952
For examples of the thermal [2+2] cycloaddition
of bis-allenes, see:
44a
Aubert P.
Princet B.
Pornet J.
Synth. Commun.
1997,
27:
2615
44b
Shimizu T.
Sakamaki K.
Kamigata N.
Tetrahedron
Lett.
1997,
38:
8529
44c
Jiang X.
Cheng X.
Ma S.
Angew.
Chem. Int. Ed.
2006,
45:
8009
For palladium-catalyzed [2+2] cycloadditions
of the two allenic internal double bonds of bis-allenes, see:
44d
Kang S.-K.
Baik T.-G.
Kulak AN.
Ha Y.-H.
Lim Y.
Park J.
J. Am. Chem. Soc.
2000,
122:
11529
44e
Hong Y.-T.
Yoon S.-K.
Kang S.-K.
Yu C.-M.
Eur. J. Org. Chem.
2004,
4628
44f See also ref. 44c.
For gold-catalyzed [2+2] cycloadditions
of the two allenic internal double bonds of bis-allenes, see:
44g
Kim SM.
Park JH.
Kang YK.
Chung YK.
Angew.
Chem. Int. Ed.
2009,
48:
4532
For nickel-catalyzed intermolecular [2+2] cycloadditions
of allenes, see:
44h
Saito S.
Hirayama K.
Kabuto C.
Yamamoto Y.
J. Am. Chem. Soc.
2000,
122:
10776
45a
Tanaka K.
Takamoto N.
Tezuka Y.
Kato M.
Toda F.
Tetrahedron
2001,
57:
3761
45b
Toda F.
Tanaka K.
Sano I.
Isozaki T.
Angew. Chem. Int. Ed. Engl.
1994,
33:
1757
45c
Sugimoto Y.
Hanamoto T.
Inanaga J.
Appl. Organomet.
Chem.
1995,
9:
369
45d
Inanaga J.
Sugimoto Y.
Hanamoto T.
Tetrahedron
Lett.
1992,
33:
7035
45e
Ezcurra JE.
Moore HW.
Tetrahedron
Lett.
1993,
34:
6177
45f
Braverman S.
Duar Y.
J. Am. Chem. Soc.
1990,
112:
5830
45g
Höhn J.
Weyerstahl P.
Chem.
Ber.
1983,
116:
808
45h
Staab HA.
Draeger B.
Chem. Ber.
1972,
105:
2320
45i
Bowes CM.
Montecalvo DF.
Sondheimer F.
Tetrahedron Lett.
1973,
3181
45j
Ben-Efraim DA.
Sondheimer F.
Tetrahedron
Lett.
1963,
313
46 For the preparation of allenes
via the [2,3]-sigmatropic rearrangement of propargyl
phosphinites, see: Hashmi ASK.
Synthesis of Allenes by Isomerization Reactions, In Modern Allene Chemistry
Vol.
1:
Krause N.
Hashmi ASK.
Wiley-VCH;
Weinheim:
2004.
p.3-50
The tandem formation and intramolecular [4+2] cycloaddition
of 1-phosphinyl-1-vinylallenes, triggered by the [2,3]-sigmatropic
rearrangement of the corresponding propargyl phosphinites, has been
reported, see:
47a
Okamura WH.
Curtin ML.
Synlett
1990,
1
47b
Curtin ML.
Okamura WH.
J.
Org. Chem.
1990,
55:
5278
48a
Kitagaki S.
Okumura Y.
Mukai C.
Tetrahedron Lett.
2006,
47:
1849
48b
Kitagaki S.
Okumura Y.
Mukai C.
Tetrahedron
2006,
62:
10311
49 The production of 67 (X = PPh2,
R = H) from 64a was described
in a review article by Grissom et al.; however, no original manuscript
dealing with the details of this reaction is available: Grissom JW.
Gunawardena GU.
Klingberg D.
Huang D.
Tetrahedron
1996,
52:
6453
50
Sonogashira K.
Tohda Y.
Hagihara N.
Tetrahedron
Lett.
1975,
4467
51
Kitagaki S.
Katoh K.
Ohdachi K.
Takahashi Y.
Shibata D.
Mukai C.
J. Org. Chem.
2006,
71:
6908
52
Kitagaki S.
Ohdachi K.
Katoh K.
Mukai C.
Org. Lett.
2006,
8:
95
53a
Myers AG.
Zheng B.
J.
Am. Chem. Soc.
1996,
118:
4492
53b
Myers AG.
Zheng B.
Org. Synth.
1998,
76:
178
54
Hakuba H.
Kitagaki S.
Mukai C.
Tetrahedron
2007,
63:
12639
55
Brown AC.
Carpino LA.
J. Org. Chem.
1985,
50:
1749
56
Movassaghi M.
Ahmad OK.
J. Org. Chem.
2007,
72:
1838
For other examples of allene-yne
cycloisomerizations, see:
57a
Brummond KM.
Chen H.
Sill P.
You L.
J. Am. Chem. Soc.
2002,
124:
15186
57b
Brummond KM.
Mitasev B.
Org. Lett.
2004,
6:
2245
57c
Shibata T.
Takasue Y.
Kadowaki S.
Takagi K.
Synlett
2003,
268
57d
Jiang X.
Ma S.
J. Am. Chem. Soc.
2007,
129:
11600
58
Kinderman SS.
van Maarseveen JH.
Schoemaker HE.
Hiemstra H.
Rutjes FPJT.
Org. Lett.
2001,
3:
2045
59
Mukai C.
Itoh R.
Tetrahedron Lett.
2006,
47:
3971
For examples of allene-ene cycloisomerizations,
see:
60a
Makino T.
Itoh K.
Tetrahedron Lett.
2003,
44:
6335
60b
Brummond KM.
Chen H.
Mitasev B.
Casarez AD.
Org. Lett.
2004,
6:
2161
60c See also ref. 30
61
Fürstner A.
Langemann K.
J. Am. Chem. Soc.
1997,
119:
9130
For other examples of bis-allene
cycloisomerizations, see:
62a
Ma S.
Lu P.
Lu L.
Hou H.
Wei J.
He Q.
Gu Z.
Jiang X.
Jin X.
Angew. Chem. Int. Ed.
2005,
44:
5275
62b
Lu P.
Ma S.
Org. Lett.
2007,
9:
5319
62c
Ma S.
Lu L.
Chem. Asian J.
2007,
2:
199
62d
Lu P.
Ma S.
Org. Lett.
2007,
9:
2095
63 For the metal-mediated synthesis
of medium-sized rings, see: Yet L.
Chem.
Rev.
2000,
100:
2963
For recent reviews, see:
64a
Carson CA.
Kerr MA.
Chem.
Soc. Rev.
2009,
38:
3051
64b
Rubin M.
Rubina M.
Gevorgyan V.
Chem.
Rev.
2007,
107:
3117
64c
Yu M.
Pagenkopf BL.
Tetrahedron
2005,
61:
321
64d
Rubina M.
Gevorgyan V.
Tetrahedron
2004,
60:
3129
64e
Kulinkovich OG.
Chem. Rev.
2003,
103:
2597
65a
Wender PA.
Takahashi H.
Witulski B.
J. Am. Chem. Soc.
1995,
117:
4720
65b
Wender PA.
Husfeld CO.
Langkopf E.
Love JA.
Pleuss N.
Tetrahedron
1998,
54:
7203
65c
Wender PA.
Sperandio D.
J. Org.
Chem.
1998,
63:
4164
65d
Wender PA.
Husfeld CO.
Langkopf E.
Love JA.
J.
Am. Chem. Soc.
1998,
120:
1940
65e
Wender PA.
Glorius F.
Husfeld CO.
Langkopf E.
Love JA.
J. Am. Chem. Soc.
1999,
121:
5348
65f
Wender PA.
Fuji M.
Husfeld CO.
Love JA.
Org.
Lett.
1999,
1:
137
65g
Wender PA.
Dyckman AJ.
Husfeld CO.
Kadereit D.
Love JA.
Rieck H.
J.
Am. Chem. Soc.
1999,
121:
10442
65h
Wender PA.
Zhang L.
Org. Lett.
2000,
2:
2323
65i
Wender PA.
Bi FC.
Brodney MA.
Gosselin F.
Org.
Lett.
2001,
3:
2105
65j
Wender PA.
Williams TJ.
Angew.
Chem. Int. Ed.
2002,
41:
4550
65k
Gómez FJ.
Kamber NE.
Deschamps NM.
Cole AP.
Wender PA.
Waymouth RM.
Organometallics
2007,
26:
4541
For the rhodium(I)-catalyzed asymmetric
cycloaddition of vinylcyclopropanes with alkynes, see:
66a
Wender PA.
Haustedt LO.
Lim J.
Love JA.
Williams TJ.
Yoon J.-Y.
J.
Am. Chem. Soc.
2006,
128:
6302
66b
Shintani R.
Nakatsu H.
Takatsu K.
Hayashi T.
Chem. Eur. J.
2009,
15:
8692
For mechanistic considerations,
see:
67a
Yu Z.-X.
Wender PA.
Houk KN.
J.
Am. Chem. Soc.
2004,
126:
9154
67b
Yu Z.-X.
Cheong PH.-Y.
Liu P.
Legault CY.
Wender PA.
Houk KN.
J.
Am. Chem. Soc.
2008,
130:
2378
67c
Liu P.
Cheong PH.-Y.
Yu Z.-X.
Wender PA.
Houk KN.
Angew.
Chem. Int. Ed.
2008,
47:
3939
68a
Owada Y.
Matsuo T.
Iwasawa N.
Tetrahedron
1997,
53:
11069
68b
Hayashi M.
Ohmatsu T.
Meng Y.-P.
Saigo K.
Angew. Chem. Int. Ed.
1998,
37:
837
68c
Murakami M.
Itami K.
Ubukata M.
Tsuji I.
Ito Y.
J.
Org. Chem.
1998,
63:
4
68d
Schmittel M.
Mahajan AA.
Bucher G.
Bats JW.
J. Org. Chem.
2007,
72:
2166
68e
Hiroi K.
Kato F.
Oguchi T.
Saito S.
Sone T.
Tetrahedron
Lett.
2008,
49:
3567
69 A successful example of a [RhCl(CO)2]2-catalyzed [5+2] cycloaddition
involving terminal alkyne and (E)-2-(1-ethoxycyclopropyl)vinyl
moieties was reported: See ref. 65g.
