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3
-
-
29744446597
-
-
note
-
c) Only a single enantiomer is shown for clarity, even though racemates were synthesized throughout this work.
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6
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0000923024
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L. Ghosez, R. Montaigne, A. Roussel, H. Vanlierde, P. Mollet, Tetrahedron 1971, 27, 615-633;
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17
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2842599954
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For examples of polycyclic compounds containing a cyclobutane ring not synthesized by a [2+2] cycloaddition, see: a) J. S. Swenton, K. A. Burdett, D. M. Madigan, T. Johnson, P. D. Rosso, J. Am. Chem. Soc. 1975, 97, 3428-3435;
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b) A. Padwa, L. Precedo, M. A. Semones, J. Org. Chem. 1999, 64, 4079-4088;
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0011211276
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a) We found few examples of cycloadditions of ketenes with tri- and tetrasubstituted olefins but not with indenes: D. A. Bak, W. T. Brady, J. Org. Chem. 1979, 44, 107-110.
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Bak, D.A.1
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24
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29744464835
-
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note
-
[5a] it was reported that 1-methylcyclohexene gave a 4:1 mixture of regioisomeric cyclobutanones in the [2+2] cycloaddition with ketene.
-
-
-
-
25
-
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29744453240
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Intramolecular [2+2] Cycloadditions of Ketenes and Olefins
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(Eds.: A. de Meijere, S. Blechert), Kluwer Academic Publishers, Norwell, MA
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B. Ernst, A. de Mesmaeker, H. Greuter, S. J. Veenstra, "Intramolecular [2+2] Cycloadditions of Ketenes and Olefins" in Strain and Its Implications in Organic Chemistry (Eds.: A. de Meijere, S. Blechert), Kluwer Academic Publishers, Norwell, MA, 1989, pp. 207-234;
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Ernst, B.1
De Mesmaeker, A.2
Greuter, H.3
Veenstra, S.J.4
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26
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0004297838
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Hypercube, Gainesville, USA
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CNDO calculations (HyperChem, version 5.1, Hypercube, Gainesville, USA) indicated that the largest coefficient for the HOMO of styrenes 3a and 3b is on the terminal carbon atom of the vinyl group. The [3.2.0] system should therefore be favored over the [3.1.1] one.
-
HyperChem, Version 5.1
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28
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0001740156
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Ketene Cycloadditions
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(Ed.: L. A. Paquette), Wiley, New York, chapter 2
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J. A. Hyatt, P. W. Raynolds, "Ketene Cycloadditions" in Organic Reactions, vol. 45 (Ed.: L. A. Paquette), Wiley, New York, 1994, chapter 2, pp. 162-646;
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Hyatt, J.A.1
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P. M. Donate, R. Da Silva, G. Valdo, J. Da Silva, C. Aleman, Synth. Commun. 2001, 31, 141-150.
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Donate, P.M.1
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30
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0025138989
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K. Shishido, T. Azuma, M. Shibuya, Tetrahedron Lett. 1990, 31, 219-220.
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Shishido, K.1
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31
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0000971871
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a) W. Guangzhong, I. Shimoyama, E.-I. Negishi, J. Org. Chem. 1991, 56, 6506-6507.
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Guangzhong, W.1
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32
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0642284306
-
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The authors described a [2+2] cycloaddition between an arylketene and a homobenzylic alkene which gave isomeric cyclobutanones (see also: B. B. Snider, E. Ron, B. W. Burbaum, J. Org. Chem. 1987, 52, 5413-5419).
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Snider, B.B.1
Ron, E.2
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33
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29744470519
-
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New Polycyclic Indanylimidazoles with Alpha2 Adrenergic Activity, WO 85698, 2001
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b) While this work was in progress, Orion Corporation published a patent application in which compounds related to 1 were claimed. In this application, however, it was not clear how the 1,2,2a,7-tetrahydrocyclobut[a]indene skeleton had been prepared. Moreover, neither experimental protocols nor characterization data were provided to support structure identification: Orion Corporation, New Polycyclic Indanylimidazoles with Alpha2 Adrenergic Activity, WO 85698, 2001; Chem. Abstr. 2001, 135, 357928.
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Chem. Abstr.
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35
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0005933054
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Attempts at generating ketene 3 by dehydrohalogenation (W. T. Brady, Y. F. Giang, J. Org. Chem. 1985, 50, 5177)
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(1985)
J. Org. Chem.
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Brady, W.T.1
Giang, Y.F.2
-
36
-
-
0003434876
-
-
or elimination of TsOH (W. T. Brady, A. P. Marchand, Y. F. Giang, A.-H. Wu, Synthesis 1987, 395-396) failed completely.
-
(1987)
Synthesis
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-
Brady, W.T.1
Marchand, A.P.2
Giang, Y.F.3
Wu, A.-H.4
-
37
-
-
29744461827
-
Preparation of Ketenes
-
Wiley & Sons, New York, chapter 3
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For a review on methods used to generate ketenes, see: T. T. Tidwell, "Preparation of Ketenes" in Ketenes, Wiley & Sons, New York, 1995, chapter 3.
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Ketenes
-
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Tidwell, T.T.1
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38
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13444310602
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See also: M. Murakami, I. Usui, M. Hasegawa, T. Matsuda, J. Am. Chem. Soc. 2005, 127, 1366-1367.
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Murakami, M.1
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39
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0035943267
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A. D. Allen, M. F. Fenwick, H. Henry-Riyad, T. T. Tidwell, J. Org. Chem. 2001, 66, 5759-5765.
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Allen, A.D.1
Fenwick, M.F.2
Henry-Riyad, H.3
Tidwell, T.T.4
-
40
-
-
29744452526
-
-
note
-
4 gave 10 as the sole product (89% yield). Analytical data for the diester 8 and diol 10 are given in the Supporting Information. The stereochemical relationship between the chains was established by NOE experiments.
-
-
-
-
41
-
-
29744444094
-
-
note
-
Treatment of 2b with EtONa/EtOH also returned the indane as a mixture of isomers (8/9 = 6:4).
-
-
-
-
42
-
-
84989473405
-
-
An example of a bicyclo[3.2.0]heptane-type derivative that ring-opens without activation by a 1,3-dicarbonyl group: C.-S. Hwang, W. Reusch, Synthesis 1989, 428-434.
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(1989)
Synthesis
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-
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Hwang, C.-S.1
Reusch, W.2
-
43
-
-
29744441132
-
-
note
-
The most obvious way to avoid having a reactive 1,3-dicarbonyl group in the cycloadduct would be to perform the cycloaddition using precursors such as 39 (see below). Unfortunately, the cycloaddition failed (see Supporting Information for characterization of 39) which highlighted the importance of ketene activation by the ester function. (Chemical Equation Presented)
-
-
-
-
44
-
-
29744434865
-
-
note
-
Both isomers were separated by chromatography on silica gel (cf. Exp. Sect.).
-
-
-
-
45
-
-
29744463807
-
-
note
-
Reduction of 2b with DIBAL produced 12-endo/exo = 80:20 (60% combined yield). The stereogenic centre at C-1 was destroyed during the synthesis of 1.
-
-
-
-
46
-
-
29744446596
-
-
note
-
The various methods used are summarized in the Supporting Information.
-
-
-
-
47
-
-
29744450062
-
-
note
-
Although a triphenylmethyl protecting group was introduced with a better regioselectivity than a pivaloyl or a TBDMS group (see Supporting Information), its high molecular weight and sensitivity towards acids or hydrogenolysis were deemed prohibitive.
-
-
-
-
49
-
-
29744431845
-
-
note
-
a) The use of metal hydrides as reducing agents gave the endoalcohol preferentially whatever the protecting group "P" on the primary alcohol. (Chemical Equation Presented)
-
-
-
-
51
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0041807380
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W. P. Griffith, S. V. Ley, G. P. Whitcombe, A. D. White, J. Chem. Soc. Chem. Commun. 1987, 1625-1627;
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Griffith, W.P.1
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52
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0027997412
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S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639-666.
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Ley, S.V.1
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54
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0030458106
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For concomitant reduction of Inflates and double bonds, see: D. Comins, Y. Zhang, J. Am. Chem. Soc. 1996, 118, 12248-12249.
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Comins, D.1
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55
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29744435032
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note
-
Chromatographic separation proved impractical for the alcohol 33, the ester 38 and the final imidazoline 1.
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57
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0025183127
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b) S. Biswas, A. Ghosh, R. V. Venkateswaran, J. Org. Chem. 1990, 55, 3498-3502.
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Bartok, M.1
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Felföldi, K.3
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62
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0001375382
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The reduction in presence of Wilkinson's catalyst required prolonged heating (24 h of refluxing in ethanol). Under these conditions, no isomerization of the double bond to an intracyclic position was detected: R. C. Ronald, M. B. Gewali, B. P. Ronald, J. Org. Chem. 1980, 45, 2224-2229.
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63
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29744441714
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note
-
Selectivity of the catalytic hydrogenations was checked at almost every stage en route to 1 (see Supporting Information), but the level of exo selectivity never exceeded that obtained for 28 or 29.
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65
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37049106917
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J. Andrieux, D. H. R. Barton, H. Patin, J. Chem. Soc., Perkin Trans. 1 1977, 359-363.
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P. K. Ruprah, J.-P. Cros, J. E. Pease, W. G. Whittingham, J. M. J. Williams, Eur. J. Org. Chem. 2002, 18, 3145-3152.
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0-catalyzed methylation, see: M. D. Lord, J. T. Negri, L. A. Paquette, J. Org. Chem. 1995, 60, 191-195.
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72
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29744463072
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-
note
-
We could not prepare the enol triflate from the keto ester 2b. We believe that a competing retro-cyclization might be interfering. (Chemical Equation Presented)
-
-
-
-
73
-
-
29744452310
-
-
note
-
α and the methyl group at C-2a). (Chemical Equation Presented)
-
-
-
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75
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37049082473
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b) R. M. Bullock, B. J. Rappoli, J. Chem. Soc., Chem. Commun. 1989, 19, 1447-1448.
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Bullock, R.M.1
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76
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0030607168
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Compound 28 did not react with Schwartz's reagent in THF or toluene, even upon heating: P. Wipf, H. Jahn, Tetrahedron 1996, 52, 12853-12910;
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Wipf, P.1
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S. Ballenweg, R. Gleiter, W. Krätschmer, Tetrahedron Lett. 1993, 34, 3737-3740.
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Ballenweg, S.1
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0344361777
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2H, various temperatures), only traces of the reduced material were formed (<5% by HPLC): H. C. Brown, K.J. Murray, Tetrahedron 1986, 42, 5497-5504.
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Brown, H.C.1
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0003874065
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(Ed.: B. Marciniec), Pergamon Press, Elmsford, NY
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4 as the catalyst: B. Marciniec, J. Gulinski, W. Urbaniak, Z. W. Kornetka, Comprehensive Handbook on Hydrosilylation (Ed.: B. Marciniec), Pergamon Press, Elmsford, NY, 1992, pp. 533-544;
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Marciniec, B.1
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Wiley & Sons, New York
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Brook, M.A.1
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83
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29744468089
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note
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Work aimed at reducing 28 in an exo-selective manner is still in progress.
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84
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0000516949
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G. Neef, U. Eder, G. Sauer, J. Org. Chem. 1981, 46, 2824-2826.
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Neef, G.1
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|