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For reviews covering this field of research, see: Lu, X.; Du, Y.; Lu, C. Pure Appl. Chem. 2005, 77, 1985-1990
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references therein
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Han, X.; Wang, Y.; Zhong, F.; Lu, Y. J. Am. Chem. Soc. 2011, 133, 1726-1729 and references therein
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Han, X.1
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79956145508
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This nomenclature is used to allow the comparison between different methodologies and is not intended to account rigorously for the correct mechanisms
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This nomenclature is used to allow the comparison between different methodologies and is not intended to account rigorously for the correct mechanisms.
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13
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77956464073
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Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447-5674
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77956367693
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For selected very recent papers, see:;, and references therein
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For selected very recent papers, see: Wang, Q.-G.; Zhu, S.-F.; Ye, L.-W.; Zhou, C.-Y.; Sun, X.-L.; Tang, Y.; Zhou, Q.-L. Adv. Synth. Catal. 2010, 352, 1914-1919 and references therein
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Wang, Q.-G.1
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Sun, X.-L.5
Tang, Y.6
Zhou, Q.-L.7
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Núñez, A.; Martín, M. R.; Fraile, A.; García Ruano, J. L. Chem. - Eur. J. 2010, 16, 5443-5453
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16
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0001282076
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For the pioneer contribution of Padwa with terminal electron-poor alkenes
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For the pioneer contribution of Padwa with terminal electron-poor alkenes, see: Padwa, A.; Yeske, P. E. J. Am. Chem. Soc. 1988, 110, 1617-1618
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Padwa, A.1
Yeske, P.E.2
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20
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Reviews on sulfone chemistry
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Reviews on sulfone chemistry: Katritzky, A. R.; Piffl, M.; Lang, H.; Anders, E. Chem. Rev. 1999, 99, 665-722
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Katritzky, A.R.1
Piffl, M.2
Lang, H.3
Anders, E.4
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El-Awa, A.1
Noshi, M.N.2
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Fuchs, P.L.4
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22
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79956112184
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Beak and co-worker did observe conjugated addition with highly activated β-substituted enones, but no cyclization occurred. Moreover, a competitive α- vs γ-addition pathway was observed likely due to equilibrated steps; see ref 9
-
Beak and co-worker did observe conjugated addition with highly activated β-substituted enones, but no cyclization occurred. Moreover, a competitive α- vs γ-addition pathway was observed likely due to equilibrated steps; see ref 9.
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23
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38349148300
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For reviews on phase transfer catalysis, see: Maruoka, K.; Hashimoto, T. Chem. Rev. 2007, 107, 5656-5682
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Hashimoto, T.2
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Ooi, T.; Maruoka, K. Angew. Chem., Int. Ed. 2007, 46, 4222-4266
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Ooi, T.1
Maruoka, K.2
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26
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0001301633
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Except for lithium or magnesium anion derivatives, the generation of allylic sulfone anion under racemic PTC has been sparingly studied. For selected examples
-
Except for lithium or magnesium anion derivatives, the generation of allylic sulfone anion under racemic PTC has been sparingly studied. For selected examples, see: Ogura, K.; Iihama, T.; Kiuchi, S.; Kajiki, T.; Koshikawa, O.; Takahashi, K.; Iida, H. J. Org. Chem. 1986, 51, 700-705
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Ogura, K.1
Iihama, T.2
Kiuchi, S.3
Kajiki, T.4
Koshikawa, O.5
Takahashi, K.6
Iida, H.7
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28
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79956147896
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2Na in order to generate an allylic sulfone anion; see ref 7
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2Na in order to generate an allylic sulfone anion; see ref 7.
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29
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43749091301
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We previously developed an access to allylic bromide having an acrylamide backbone through two straightforward steps involving an MBH-reaction/ bromination sequence from commercially available acrylamides; see
-
We previously developed an access to allylic bromide having an acrylamide backbone through two straightforward steps involving an MBH-reaction/ bromination sequence from commercially available acrylamides; see: Davoust, M.; Cantagrel, F.; Metzner, P.; Brière, J.-F. Org. Biomol. Chem. 2008, 6, 1981-1993
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Davoust, M.1
Cantagrel, F.2
Metzner, P.3
Brière, J.-F.4
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77952821762
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For recent developments in organocatalysis with sulfones
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For recent developments in organocatalysis with sulfones, see: Alba, A.-N. R.; Companyo, X.; Rios, R. Chem. Soc. Rev. 2010, 39, 2018-2033
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Chem. Soc. Rev.
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Alba, A.-N.R.1
Companyo, X.2
Rios, R.3
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Nielsen, M.; Jacobsen, C. B.; Holub, N.; Paixão, M. W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2010, 49, 2668-2679
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Nielsen, M.1
Jacobsen, C.B.2
Holub, N.3
Paixão, M.W.4
Jørgensen, K.A.5
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32
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0001473360
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For early use of such allylic sulfones
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For early use of such allylic sulfones, see: Nájera, C.; Mancheño, B.; Yus, M. Tetrahedron Lett. 1989, 30, 3837-3840
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(1989)
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Nájera, C.1
Mancheño, B.2
Yus, M.3
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Tanaka, K.; Horiuchi, H.; Yoda, H. J. Org. Chem. 1989, 54, 63-70
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Tanaka, K.1
Horiuchi, H.2
Yoda, H.3
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34
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79956095704
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DBDB was synthesized in one step from dibutylamine and commercially available 2,2′-bis(bromomethyl)-1,1′-biphenyl (see Experimental Section)
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DBDB was synthesized in one step from dibutylamine and commercially available 2,2′-bis(bromomethyl)-1,1′-biphenyl (see Experimental Section).
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35
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note
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Many cinchona derived phase transfer catalysts were tried but did not outperform the Maruokas catalyst. For instance, the best N- anthracenyl cinchonidinium chloride one afforded (NaOH, rt) the cyclopentene 7a in 38% ee and 55% yield. However, this family of catalysts tend to decomposition in our conditions, rendering tedious their development for this methodology.
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Bhagat, S.; Sharma, R.; Sawant, D. M.; Sharma, L.; Chakraborti, A. J. Mol. Catal. A: Chem. 2006, 244, 20
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(2006)
J. Mol. Catal. A: Chem.
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, pp. 20
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Bhagat, S.1
Sharma, R.2
Sawant, D.M.3
Sharma, L.4
Chakraborti, A.5
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