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Organic & Biomolecular Chemistry
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14, 601; (c) A. Kouridaki, T. MontaDgOnoI:n10, .1M03.V9i/eTDwo0AfOirtBica0len0Od4n6li8GnEe.
Vassilikogiannakis, Org. Lett., 2012, 14, 2374.
Acknowledgements
We would like to dedicate this article to Prof. John Gallos,
mentor and friend, on the occasion of his retirement.
The research leading to these results has received funding
from the European Research Council under the European
Union’s Seventh Framework Programme (FP7/2007-2013)/ERC
grant agreement no. 277588. We thank the Greek General
Secretariat of Research and Technology for matching (reward)
funds (KA: 4143). We also thank the Alexander S. Onassis
Public Benefit Foundation for the Ph.D. fellowship of Manolis
Sofiadis (G ZM 063-1/2016-2017).
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17 T. Montagnon, D. Kalaitzakis, M. Sofiadis and G.
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18 For examples of enedione use in asymmetric organocatalysis,
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Notes and references
1
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Benign can be defined (see ref that follows) as “a by-product,
reagent or solvent that has no known environmental risk
associated with it; for example water, low-concentration
saline, dilute ethanol, autoclaved cell mass, etc.” T. Hudlicky,
D. A. Frey, L. Koroniak, C. D. Claeboe and L. E. Brammer Jr.,
Green Chem., 1999, 1, 57.
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D. Sengupta, R. W. Pike, Chemicals from Biomass; Integrating
Bioprocesses into Chemical Production Complexes for
Sustainable Development, 2012, CRC Press, Boca Raton
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B. A. Trost, Science, 1991, 254, 1471.
P. A. Wender and B. L. Miller, Nature, 2009, 460, 197.
(a) T. Newhouse, P. S. Baran and R. W. Hoffmann, Chem. Soc.
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7
8
For a discussion on metrics, see; A. Lapkin, D. J. C. Constable,
Green Chemistry Metrics: Measuring and Monitoring
Sustainable Processes, 2008, Wiley, UK.
For reviews, see; (a) T. Montagnon, D. Kalaitzakis, M.
Triantafyllakis, M. Stratakis and G. Vassilikogiannakis, Chem.
Commun., 2014, 50, 15480; (b) T. Montagnon, D. Noutsias, I.
Alexopoulou, M. Tofi and G. Vassilikogiannakis, Org. Biomol.
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Vassilikogiannakis, Acc. Chem. Res., 2008, 41, 1001; For
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I. Ioannou and G. Vassilikogiannakis, Angew. Chem. Int. Ed.,
2017, 56, 4020; (e) E. Antonatou, K. Hoogewijs, D.
Kalaitzakis, A. Baudot, G. Vassilikogiannakis and A. Madder,
Chem. Eur. J., 2016, 22, 8457; (f) D. Kalaitzakis, M.
Triantafyllakis, M. Sofiadis, D. Noutsias and G.
Vassilikogiannakis, Angew. Chem. Int. Ed., 2016, 55, 4605; (g)
D. Kalaitzakis, D. Noutsias and G. Vassilikogiannakis, Org.
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Noutsias, T. Montagnon and G. Vassilikogiannakis, Angew.
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19 In our own chemistry, pendent nucleophiles have frequently
been used to control regioselectivity; for examples, see; refs
8a-c.
20 For keto-ene-ester/acid examples, see; (a) J.-B. Lin, S.-M. Xu,
J.-K. Xie, H.-Y. Li and P.-F. Xu, Chem. Commun., 2015, 51,
3596; (b) W. Zhou, X. Su, M. Tao, C. Zhu, Q. Zhao and J.
Zhang, Angew. Chem. Int. Ed., 2015, 54, 14853; (c) S. Žari, M.
Kudrjashova, T. Pehk, M. Lopp and T. Kanger, Org. Lett.,
2014, 16, 1740. For amide-enen-keto/ester/acid (n = 1,2)
examples, see; (d) S. Muthusamy and V. Kesavan, Eur. J. Org.
Chem., 2019, 4046; (e) B.-X. Xiao, W. Du and Y.-C. Chen, Adv.
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H. Lauridsen, E. H. Iversen, B. S. Donslund and K. A.
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21 Very recently
a paper describing the formal [3+2]-
cycloaddition between (E)-ethyl 4-oxopent-2-enoate and 2-
enals for an elegant synthesis of Corey’s lactone has been
published, see; N. Umekubo, Y. Suga and Y. Hayashi, Chem.
Sci., 2020, 11, 1205.
9
(a) D. Kalaitzakis, M. Triantafyllakis, I. Alexopoulou, M.
Sofiadis and G. Vassilikogiannakis, Angew. Chem. Int. Ed.,
2014, 53, 13201; (b) D. Noutsias, I. Alexopoulou, T.
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