Please Rd So Cn oA tda vd aj un sc te ms argins
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to give stable
in high yield. Treating 5a with 1-phenyl-2- cascade involving α,β-unsaturated aldDeOhI:y1d0e.1.039T/hCi6sRA0n3o5v71eJl
triphenylphosphoranylidene)-ethanone led to an apparent approach broadens the useful scope of sequential dual
5
a
9
(
16
Wittig-oxa-Michael process, affording the multi-functionalized catalysis. Further study of asymmetric domino reactions
tetrahydrofuran 10 with three chiral centers.
involving NHC-amine catalysis are underway in our laboratory.
Acknowledgements
We are grateful for financial support from NSFC (21302016,
8
1573588 and 81573589), the Science & Technology
Department of Sichuan Province (2014JQ0020) and the
Foundation for the Author of National Excellent Doctoral
Dissertation of PR China (201487).
Notes and references
1
For recent reviews on the asymmetric synthesis of trifluoro-
methylated compounds, see: (a) T. Furuya, A. S. Kamlet and
T. Ritter, Nature, 2011, 473, 470-477; (b) J. Nie, H.-C. Guo, D.
Cahard and J.-A. Ma, Chem. Rev., 2011, 111, 455-529; (c) O.
A. Tomashenko and V. V. Grushin, Chem. Rev., 2011, 111
,
4
8
475-4521; (d) A. Studer, Angew. Chem., Int. Edit., 2012, 51
,
Scheme 4 Proposed Mechanism of the Asymmetric Cascade Reaction.
950-8958; (e)T. Liang, C. N. Neumann and T. Ritter, Angew.
Chem., Int. Edit., 2013, 52, 8214-8264; (f) E. Merino and C.
Nevado, Chem. Soc. Rev., 2014, 43, 6598-6608.
2
For recent reviews on the applications of fluorine in
medicinal chemistry, see: (a) C. Isanbor and D. O'Hagan, J.
Fluorine Chem., 2006, 127, 303-319; (b) K. L. Kirk, J. Fluorine
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Moore, S. Swallow and V. Gouverneur, Chem. Soc. Rev., 2008,
37, 320-330; (f) J. Wang, M. Sánchez-Roselló, J. Luis Aceña, C.
del Pozo, A. E. Sorochinsky, S. Fustero, V. A. Soloshonok and
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Eastman, M. D. Hill, D. J. Donnelly and N. A. Meanwell, J.
Med. Chem., 2015, 58, 8315-8359.
For recent reviews on the synthesis of chiral γ-butyrolactone
derivatives, see: (a) M. Seitz and O. Reiser, Curr. Opin. Chem.
3
Biol., 2005,
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, 285-292; (b) S. Gil, M. Parra, P. Rodriguez and J.
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Kitson, A. Millemaggi and R. J. K. Taylor, Angew. Chem. Int.
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4
5
(a) C. Burstein and F. Glorius, Angew. Chem., Int. Edit., 2004,
43, 6205-6208; (b) K. Hirano, I. Piel and F. Glorius, Adv. Synth.
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(a) C. Burstein, S. Tschan, X. Xie and F. Glorius, Synthesis,
2
006, 2418-2439; (b) Y. Matsuoka, Y. Ishida and K. Saigo,
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Ishida, D. Sasaki and K. Saigo, Chem.-Eur. J., 2008, 14, 9215-
Scheme 5 Chemical Transformation of 5a.
9
222; (d) R. B. Strand, T. Helgerud, T. Solvang, A. Dolva, C. A.
Sperger and A. Fiksdahl, Tetrahedron-Asymmetry, 2012, 23
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Z. Fu, J. Xu, T. Zhu, W. W. Y. Leong and Y. R. Chi, Nat. Chem.,
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For some other approaches to CF
,
1
Conclusions
6
7
2
5
In conclusion, we have developed an efficient and practical
one-pot cascade process that delivers synthetically useful,
multi-functionalized chiral hydrogenated γ-butyrolactone
3
-substituted chiral γ-
butyrolactone derivatives, see: (a) P. V. Ramachandran, K. J.
Padiya, V. Rauniyar, M. V. R. Reddy and H. C. Brown,
Tetrahedron Lett., 2004, 45, 1015-1017; (b) P. Bravo, M.
Frigerio, A. Melloni, W. Panzeri, C. Pesenti, F. Viani and M.
Zanda, Eur. J. Org. Chem., 2002, 1895-1902; (c) Y. Komatsu, F.
derivatives
featuring
a
CF
3
-substituted
quaternary
stereocenter in good yield with high stereoselectivity. The
process comprises a highly chemoselective NHC-catalyzed
intermolecular cross-Benzoin reaction of aromatic aldehydes
with trifluoroacetaldehyde ethyl hemiacetal; followed by a
Sasaki, S. Takei and T. Kitazume, J. Org. Chem., 1998, 63
,
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058-8061.
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