Communication
ChemComm
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Notes and references
1 T. E. Nielsen and S. L. Schreiber, Angew. Chem., Int. Ed., 2008, 47, 48
and references cited therein.
2 M.-J. Kim, W. J. Hennen, H. M. Sweers and C.-H. Wong, J. Am. Chem.
Soc., 1988, 110, 6481; H. J. M. Gijsen, L. Qiao, W. Fitz and C.-
H. Wong, Chem. Rev., 1996, 96, 443.
10 A. D. Daniel, I. Campeotto, M. W. van der Kamp, A. H. Bolt, C. H.
Trinh, S. E. V. Phillips, A. R. Pearson, A. Nelson, A. J. Mulholland
and A. Berry, ACS Chem. Biol., 2014, 9, 1025.
11 Product 1aa obtained in Table 1 was mainly (470%) the cyclic forms
after initial isolation/purification. The ratio of the cyclic form to the
corresponding acyclic, C2 symmetric, achiral linear form varied
depending on the aldehyde used in the reaction and on other
factors such as time kept after isolation. (See ESI‡). Cyclic hemi-
acetals are often in equilibrium with the corresponding open chain,
linear forms.
12 b-Proline has been used for Mannich-type reactions of ketones via
in situ-generation of enamines, but has not been used in reactions of
pyruvates. See: (a) H. Zhang, M. Mifsud, F. Tanaka and C. F. Barbas
III, J. Am. Chem. Soc., 2006, 128, 9630; (b) H. Zhang, S. Mitsumori,
N. Utsumi, M. Imai, N. Garcia-Delgado, M. Mifsud, K. Albertshofer,
P. H.-Y. Cheong, K. N. Houk, F. Tanaka and C. F. Barbas III, J. Am.
Chem. Soc., 2008, 130, 875.
13 D. Zhang, S. Johnson, H.-L. Cui and F. Tanaka, Asian J. Org. Chem.,
2014, 3, 391.
14 For the b-proline-catalysis to give 1aa, CH3CN was the best solvent
among those tested. Solvent screen results under the conditions of
Table 1, entry 7: 1aa was obtained in a range of 6–15% in toluene,
CH2Cl2, CHCl3, DMSO, DMF, THF, 1,4-dioxane, and 2-PrOH; no
formation of 1aa was detected in CH3CN–H2O (3 : 1).
15 Z. Xu, L. Liu, K. Wheeler and H. Wang, Angew. Chem., Int. Ed., 2011,
50, 3484.
16 Note that for many of 6-membered hemiacetals (such as carbo-
hydrates including glucose), the cyclic form is stable and they do not
behave as typical aldehydes: (a) B. Voigt, U. Scheffler and R. Mahrwald,
Chem. Commun., 2012, 48, 5304; (b) B. Voigt, A. Anastassia and
R. Mahrwald, Tetrahedron, 2013, 69, 4302.
17 Fluoropyran derivatives include enzyme inhibitors and other bio-
functional molecules: (a) C.-S. Tsaai, H.-Y. Yen, M.-I. Lin, T.-I. Tsai,
S.-Y. Wang, W.-I. Huang, T.-L. Hsu, Y.-S. E. Cheng, J.-M. Fang and
C.-H. Wong, Proc. Natl. Acad. Sci. U. S. A., 2013, 110, 2466; (b) J.-H.
Kim, R. Resende, T. Wennekes, H.-M. Chen, N. Bance, S. Buchini,
A. G. Watts, P. Pilling, V. A. Streltsov, M. Petric, R. Liggins, S. Barrett,
J. L. McKimm-Breschkin, M. Niikura and S. G. Withers, Science,
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18 Fluoropyran derivatives as building blocks: (a) Y. Zhang, J. Gaekwad,
M. A. Wolfert and G.-J. Boons, Chem. – Eur. J., 2008, 14, 558;
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3 (a) P. Dambruoso, A. Masai and A. Dondoni, Org. Lett., 2005, 7, 4657;
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4 Reaction methods used on a-ketoacid derivatives that are equal or
larger than 2-ketobutanoic acid derivatives often do not work for the
reactions of 2-ketopropionic acid (i.e., pyruvic acid) derivatives. See:
J.-M. Vincent, C. Margottin, M. Berlande, D. Cavagnat, T. Buffeteau
and Y. Landais, Chem. Commun., 2007, 4782.
5 Because of the difficulty to control the nucloephilic and electrophilic
reactivities of pyruvates, pyruvate surrogates and precursors have
often been used. See: (a) D. Enders and T. Gasperi, Chem. Commun.,
2007, 88; (b) R. Winzar, J. Philip and M. J. Kiefel, Synlett, 2010, 583.
6 Reactions of a-ketoacid derivatives that are equal or larger than
2-ketobutanoic acid derivatives: (a) D. Lee, S. G. Newman and
M. S. Taylor, Org. Lett., 2009, 11, 5486; (b) G. Lu, H. Morimoto,
S. Matsunaga and M. Shibasaki, Angew. Chem., Int. Ed., 2008,
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Chem., Int. Ed., 2009, 48, 3353; (d) A. Nakamura, S. Lectard,
D. Hashizume, Y. Hamashima and M. Sodeoka, J. Am. Chem. Soc.,
2010, 132, 4036; (e) O. El-Sepelgy and J. Mlynarski, Adv. Synth. Catal.,
2013, 355, 281; ( f ) L. C. Akullian, M. L. Snapper and A. H. Hoveyda,
J. Am. Chem. Soc., 2006, 128, 6532; (g) J. Sedelmeier, T. Hammerer
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and V. H. Rawal, Chem. Commun., 2010, 46, 904; (i) H. Li, B. Wang
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A. Alexakis, Angew. Chem., Int. Ed., 2012, 51, 794; (k) A. Lee and
K. A. Scheidt, Angew. Chem., Int. Ed., 2014, 53, 7594; (l) See also
ref. 4.
7 Selected reports on the synthesis of dihydro- and tetrahydropyrans:
(a) J. Magano, Chem. Rev., 2009, 109, 4398; (b) H. Ishikawa,
S. Sawano, Y. Yasui, Y. Shibata and Y. Hayashi, Angew. Chem., Int.
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Jacobsen, Angew. Chem., Int. Ed., 1999, 38, 2398; (e) Y. Yamashita,
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Rawal, J. Am. Chem. Soc., 2005, 127, 1336; (g) N. Momiyama,
H. Tabuseand and M. Terada, J. Am. Chem. Soc., 2009, 131, 12882;
(h) J. Guin, C. Rabalakos and B. List, Angew. Chem., Int. Ed., 2012,
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H. Schneider, B. Seilheimer and L. Turski, J. Med. Chem., 2005,
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H. Nemoto, N. Toyooka and Y. Matsuya, Org. Lett., 2012, 14, 3510.
8 Selected cascade reactions: (a) C. Grondal, M. Jeanty and D. Enders, 20 (a) A. Picot, A. D’Aleo, P. L. Baldeck, A. Grichine, A. Duperray,
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9 Reactions of b,g-unsaturated a-ketoesters with aldehydes or ketones
to afford dihydropyrans: (a) S.-L. Zhao, C.-W. Zheng, H.-F. Wang and
G. Zhao, Adv. Synth. Catal., 2009, 351, 2811; (b) Z. Xu, L. Liu,
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14884 | Chem. Commun., 2014, 50, 14881--14884
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