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See also: Pellissier, H. Tetrahedron 2006, 62, 1619-1665 and 2143-2173.
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Pellissier, H.1
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(a) Ishikawa, T.; Kadoya, R.; Arai, M.; Takahashi, H.; Kaishi, Y.; Mizuta, T.; Yoshikai, K.; Saito, S. J. Org. Chem. 2001, 66, 8000-8009.
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Yoshikai, K.7
Saito, S.8
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4
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17444402508
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See also: Ishikawa. T.; Miyahara, T.; Asakura, M.; Higuchi, S.; Miyauchi, Y.; Saito, S. Org. Lett. 2005, 7, 1211-121. We succeeded in achieving domino processes leading to benzofurans from cyclohexane-1,3-diones in one pot in which 13 elementary processes were operating.
-
See also: Ishikawa. T.; Miyahara, T.; Asakura, M.; Higuchi, S.; Miyauchi, Y.; Saito, S. Org. Lett. 2005, 7, 1211-121. We succeeded in achieving domino processes leading to benzofurans from cyclohexane-1,3-diones in one pot in which 13 elementary processes were operating.
-
-
-
-
5
-
-
33846223219
-
-
Since domino reactions are defined as processes of making two or more bonds in which the subsequent reactions take place at the functionalities obtained in the former step, the processes presented in this work are not necessarily the domino processes. For the definition of the domino processes, see ref 1
-
Since domino reactions are defined as processes of making two or more bonds in which the subsequent reactions take place at the functionalities obtained in the former step, the processes presented in this work are not necessarily the domino processes. For the definition of the domino processes, see ref 1.
-
-
-
-
6
-
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8244225873
-
-
For review, see:, Trost, B. M, Fleming, I, Eds, Pergamon: Oxford, Chapter 2.3
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For review, see: Jones, A. B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 7, Chapter 2.3.
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Jones, A.B.1
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7
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4344651796
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For review, see
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For review, see: Merino, P.; Tejero, T. Angew. Chem., Int. Ed. 2004, 43, 2995-2997.
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0032054562
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For recent examples, see: a
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For recent examples, see: (a) Hoffmann, T.; Zhong, G.; List, B.; Shabat, D.; Anderson, J.; Gramatikova, S.; Lerner, R.; Barbas, C. F., III J. Am. Chem. Soc. 1998, 120, 2768-2779.
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(d) Yoshikawa, N.; Kumagai, N.; Matsunaga, S.; Moll, G.; Ohshima, T.; Suzuki, T.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 2466-2467.
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Suzuki, T.6
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(e) Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367-3368.
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3142697747
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(f) Tang, Z.; Yang, Z.-H.; Cun, L.-Z.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z. Org. Lett. 2004, 6, 2285-2287.
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23044470281
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Evans, D. A.; Glorius, F.; Burch, J. D. Org. Lett. 2005, 7, 3331-3333.
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Evans, D.A.1
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15
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33846218194
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For reviews, see: g, Trost, B. M, Fleming, I, Eds, Pergamon: Oxford, Chapter 2.4
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For reviews, see: (g) Hassner, A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, Chapter 2.4.
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0000732727
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McElvain1
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(d) Finley, K. T. Chem. Rev. 1964, 64, 573-589.
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Finley, K.T.1
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25
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0000166356
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It was reported that when LDA was employed for generating chiral enolates from N-(benzyloxyacetyl)- or N-(tert- butyldimethylsilyloxyacetyl)-oxazolidinone followed by addition of neryl bromide, no alkylation proceeded at all for the TBDMS-protection case and only 20% yield of alkylated product was obtained for the benzyl-protection case. However, when other chiral auxiliary such as (-)-ephedrine-derived imidazolidinone was employed, its N-(benzyloxyacetyl) derivative led to 49% yield of alkylated product (LDA, neryl bromide), see: Cardillo, G.; Orena, M.; Romero, M.; Sandri, S. Tetrahedron 1989, 45, 1501-1508.
-
It was reported that when LDA was employed for generating chiral enolates from N-(benzyloxyacetyl)- or N-(tert- butyldimethylsilyloxyacetyl)-oxazolidinone followed by addition of neryl bromide, no alkylation proceeded at all for the TBDMS-protection case and only 20% yield of alkylated product was obtained for the benzyl-protection case. However, when other chiral auxiliary such as (-)-ephedrine-derived imidazolidinone was employed, its N-(benzyloxyacetyl) derivative led to 49% yield of alkylated product (LDA, neryl bromide), see: Cardillo, G.; Orena, M.; Romero, M.; Sandri, S. Tetrahedron 1989, 45, 1501-1508.
-
-
-
-
26
-
-
33846219083
-
-
As indicated in ref 8, Evans substrate such as N-(tert- butyldimethylsilyloxyacetyl)oxazolidinone did not lead to any alkylation product at all (LDA, neryl bromide, THF). Our observation for 1c similar to that previous case may be ascribed to the same cause, which is not completely clear at present. We must await future systematic studies for elucidating the exact nature of the hydroxyacetone enolates concerned.
-
As indicated in ref 8, Evans substrate such as N-(tert- butyldimethylsilyloxyacetyl)oxazolidinone did not lead to any alkylation product at all (LDA, neryl bromide, THF). Our observation for 1c similar to that previous case may be ascribed to the same cause, which is not completely clear at present. We must await future systematic studies for elucidating the exact nature of the hydroxyacetone enolates concerned.
-
-
-
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27
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0001319849
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Schinzer, D.; Limberg, A.; Böhm, O. M. Chem. Eur. J. 1996, 2, 1477-1482.
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Schinzer, D.1
Limberg, A.2
Böhm, O.M.3
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28
-
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33846226015
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-
2, 0 °C) to give bis-[(2S,3S)-3-tert- butyldiphenylsiloxy-4,4-dimethyl]oxolan-2-yl ether. We are now trying to convert this dimer (hemiacetal anhydride) to 23.
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2, 0 °C) to give bis-[(2S,3S)-3-tert- butyldiphenylsiloxy-4,4-dimethyl]oxolan-2-yl ether. We are now trying to convert this dimer (hemiacetal anhydride) to 23.
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-
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29
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0030767001
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(a) Nicolaou, K. C.; Ninkovic, S.; Sarabia, F.; Vourloumis, D.; He, Y.; Vallberg, H.; Finlay, M. R. V.; Yang, Z. J. Am. Chem. Soc. 1997, 119, 7974-7991.
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Nicolaou, K.C.1
Ninkovic, S.2
Sarabia, F.3
Vourloumis, D.4
He, Y.5
Vallberg, H.6
Finlay, M.R.V.7
Yang, Z.8
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30
-
-
0030669587
-
-
(b) Meng, D.; Bertinato, P.; Balog, A.; Su, D.-S.; Kamenecka, T.; Sorensen, E. J.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10073-10092.
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Meng, D.1
Bertinato, P.2
Balog, A.3
Su, D.-S.4
Kamenecka, T.5
Sorensen, E.J.6
Danishefsky, S.J.7
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31
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0030894922
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(c) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 523-524.
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Angew. Chem., Int. Ed. Engl
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, pp. 523-524
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Schinzer, D.1
Limberg, A.2
Bauer, A.3
Böhm, O.M.4
Cordes, M.5
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32
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0032869834
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(d) Schinzer, D.; Bauer, A.; Böhm, O. M.; Limherg. A.; Cordes, M. Chem. Eur. J. 1999, 5, 2483-2491.
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Schinzer, D.1
Bauer, A.2
Böhm, O.M.3
Limherg, A.4
Cordes, M.5
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33
-
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2942604950
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(e) Storer, R. I.; Takemoto, T.; Jackson, P. S.; Brown, D. S.; Baxendale, I. R.; Ley, S. V. Chem. Eur. J. 2004, 10, 2529-2547.
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Chem. Eur. J
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Storer, R.I.1
Takemoto, T.2
Jackson, P.S.3
Brown, D.S.4
Baxendale, I.R.5
Ley, S.V.6
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34
-
-
4644242591
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-
For synthesis of the epothilone D segment from neryl halide, see
-
For synthesis of the epothilone D segment from neryl halide, see: Scheid, G.; Ruijter, E.; Konarzycka-Bessler, M.; Bornscheuer, U. T.; Wessjohann, L. A. Tetrahedron: Asymmetry 2004, 15, 2861-2869.
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Tetrahedron: Asymmetry
, vol.15
, pp. 2861-2869
-
-
Scheid, G.1
Ruijter, E.2
Konarzycka-Bessler, M.3
Bornscheuer, U.T.4
Wessjohann, L.A.5
-
35
-
-
33846230523
-
-
2 (AB quartet) for X, which tentatively led us to conclude that X contains polyalkylated products such as 34, 35, or 36, though a final decision must await further reliable structural analyses. On the basis of these considerations, the yield of the polyalkylated products was calculated to be 2.5%.
-
2 (AB quartet) for X, which tentatively led us to conclude that X contains polyalkylated products such as 34, 35, or 36, though a final decision must await further reliable structural analyses. On the basis of these considerations, the yield of the polyalkylated products was calculated to be 2.5%.
-
-
-
-
36
-
-
33846214355
-
-
Because of the higher volatility of 30, significant loss of products during evaporative workup was unavoidable. Accordingly, the yield indicated in the text was determined by NMR for a sample containing EtOAc stemmed from column chromatographic separation.
-
Because of the higher volatility of 30, significant loss of products during evaporative workup was unavoidable. Accordingly, the yield indicated in the text was determined by NMR for a sample containing EtOAc stemmed from column chromatographic separation.
-
-
-
-
37
-
-
33846264042
-
-
Structures of difficult to separate polyalkylation products (three components) were estimated to be 37 (two diastereoisomers) and 38 on the basis of NMR analysis of the mixture. Chemical yield was calculated based on these structures.
-
Structures of difficult to separate polyalkylation products (three components) were estimated to be 37 (two diastereoisomers) and 38 on the basis of NMR analysis of the mixture. Chemical yield was calculated based on these structures.
-
-
-
-
38
-
-
33846234262
-
-
For a review on alkylations of heteroatom-stabilized carbanions other than acyloins, see:, Trost, B. M, Fleming, I, Eds, Pergamon: Oxford, Chapter 1.4
-
For a review on alkylations of heteroatom-stabilized carbanions other than acyloins, see: Cheshire, D. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, Chapter 1.4.
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(1991)
Comprehensive Organic Synthesis
, vol.3
-
-
Cheshire, D.R.1
-
39
-
-
0001010896
-
-
In this series of outstanding comprehensive surveys, no description of the alkylation or allylation of acyloins is presented, see also: Evans, D. A.; Sacks, C. E.; Kleschick, W. A.; Taber, T. R. J. Am. Chem. Soc. 1979, 101, 6789-6791 in which regioselective alkylation of 2-butanone-based 3-PhS-substituted N,N-dimethylhydrazone under thermodynamically controlled conditions [KH, tert-BuOK (0.03 equiv). THF, reflux, then iodoalkane, 0 °C to rt) is described.
-
In this series of outstanding comprehensive surveys, no description of the alkylation or allylation of acyloins is presented, see also: Evans, D. A.; Sacks, C. E.; Kleschick, W. A.; Taber, T. R. J. Am. Chem. Soc. 1979, 101, 6789-6791 in which regioselective alkylation of 2-butanone-based 3-PhS-substituted N,N-dimethylhydrazone under thermodynamically controlled conditions [KH, tert-BuOK (0.03 equiv). THF, reflux, then iodoalkane, 0 °C to rt) is described.
-
-
-
-
40
-
-
0001081787
-
-
The acyloin framework is a key structural unit of many natural products, and chiral α-hydroxy ketones (acyloins) are versatile synthetic intermediates for diversified bioactive compounds, see: (a) Bel-Rhlid, R.; Fauve, A.; Veschambre, H. J. Org. Chem. 1989, 54, 3221-3223.
-
The acyloin framework is a key structural unit of many natural products, and chiral α-hydroxy ketones (acyloins) are versatile synthetic intermediates for diversified bioactive compounds, see: (a) Bel-Rhlid, R.; Fauve, A.; Veschambre, H. J. Org. Chem. 1989, 54, 3221-3223.
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41
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0001634857
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(b) Awano, K.; Yanai, T.; Watanabe, I.; Takagi, Y.; Kitahara, T.; Mori, K. Biosci. Biotechnol. Biochem. 1995, 59, 1251-1254.
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Kitahara, T.5
Mori, K.6
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43
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4544228325
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(d) Scheid, G.; Huit, W.; Ruijter, E.; Orru, R. V. A.; Henke, E.; Bornscheuer, U.; Wessjohann, L. A. Eur. J. Org. Chem. 2004, 1063-1074.
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Scheid, G.1
Huit, W.2
Ruijter, E.3
Orru, R.V.A.4
Henke, E.5
Bornscheuer, U.6
Wessjohann, L.A.7
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