Organic & Biomolecular Chemistry
Communication
with 97% ee of the remaining chiral carbon. It is noteworthy
that even though the syn/anti ratio of the Mannich adduct 5
was low (3.7 : 1), one-carbon shortened enantiomerically
enriched amino acid ester was achieved after the removal of
one chiral center.
In conclusion, we have developed a metal-free method for
the oxidative C–C cleavage of α-alkoxy aldehydes using air as
the oxidant. The reaction proceeded under mild and environ-
ment-friendly conditions within short time. Moreover, we
provided a model reaction for the synthesis of (D)-serine deriva-
tives in combination with a L-proline catalyzed Mannich reac-
tion. This simple, low-cost and environment-friendly approach
is a useful addition to the repertoire of present synthetic
strategies.
J. Zhang and Y. R. Chi, Angew. Chem., Int. Ed., 2012, 51,
1911–1914; (c) N. Havare and D. A. Plattner, Org. Lett.,
2012, 14, 5078–5081; (d) R. Lin, F. Chen and N. Jiao, Org.
Lett., 2012, 14, 4158–4161.
4 H. Sun, C. Yang, F. Gao, Z. Li and W. Xia, Org. Lett., 2013,
15, 624–627.
5 J.-A. Ma, Angew. Chem., Int. Ed., 2003, 42, 4290–4299.
6 P. Kaur, S. Pindi, W. Wever, T. Rajale and G. Li, Chem.
Commun., 2010, 46, 4330–4332.
7 B. Lygo and B. I. Andrews, Acc. Chem.Res., 2004, 37, 518–
525.
8 (a) A. Córdova, S.-i. Watanabe, F. Tanaka, W. Notz and
C. F. Barbas, J. Am. Chem. Soc., 2002, 124, 1866–1867;
(b) J. Chen, X. Lu, W. Lou, Y. Ye, H. Jiang and W. Zeng,
J. Org. Chem., 2012, 77, 8541–8548; (c) Y. Li, D.-M. Ji and
M.-H. Xu, Org. Biomol. Chem., 2011, 9, 8452–8458;
(d) M. Rueping and A. P. Antonchick, Org. Lett., 2008, 10,
1731–1734.
Acknowledgements
This work was supported by a grant from the National
Natural Science Foundation of China (NSFC No. 21072017)
and National Key Science Research Program of China (973
Program, No. 2012 CB822101) and Key Drug Innovation
Project of China (No. 2012ZX09502001–001).
9 M. J. Burk, M. F. Gross and J. P. Martinez, J. Am. Chem.
Soc., 1995, 117, 9375–9376.
10 (a) Q. Kang, Z.-A. Zhao and S.-L. You, Adv. Synth. Catal.,
2007, 349, 1657–1660; (b) C. Zhu and T. Akiyama, Adv.
Synth. Catal., 2010, 352, 1846–1850; (c) M. Rueping,
A. P. Antonchick and C. Brinkmann, Angew. Chem., Int. Ed.,
2007, 46, 6903–6906; (d) S. Zhou, S. Fleischer, K. Junge,
S. Das, D. Addis and M. Beller, Angew. Chem., Int. Ed., 2010,
49, 8121–8125; (e) C. Wang, X. Wu, L. Zhou and J. Sun,
Chem.–Eur. J., 2008, 14, 8789–8792; (f) S. Werkmeister,
S. Fleischer, K. Junge and M. Beller, Chem.–Asian, J, 2012,
7, 2562–2568; (g) Z.-Y. Xue, Y. Jiang, W.-C. Yuan and
X.-M. Zhang, Eur. J. Org. Chem., 2010, 616–619; (h) G. Li,
Y. Liang and J. C. Antilla, J. Am. Chem. Soc., 2007, 129,
5830–5831; (i) S. Guizzetti, M. Benaglia and S. Rossi, Org.
Lett., 2009, 11, 2928–2931; ( j) Q. Kang, Z.-A. Zhao and
S.-L. You, Org. Lett., 2008, 10, 2031–2034; (k) X. Xiao,
M. Liu, C. Rong, F. Xue, S. Li, Y. Xie and Y. Shi, Org. Lett.,
2012, 14, 5270–5273; (l) C. Zhu and T. Akiyama, Org. Lett.,
2009, 11, 4180–4183.
Notes and references
1 (a) C.-H. Jun, Chem. Soc. Rev., 2004, 33, 610–618;
(b) M. Tobisu and N. Chatani, Chem. Soc. Rev., 2008, 37,
300–307; (c) K. Ruhland, Eur. J. Org. Chem., 2012, 2683–
2706; (d) R. H. Crabtree, Nature, 2000, 408, 415–416.
2 (a) R.-J. Song, Y. Liu, R.-X. Hu, Y.-Y. Liu, J.-C. Wu,
X.-H. Yang and J.-H. Li, Adv. Synth. Catal., 2011, 353, 1467–
1473; (b) K. Chen, H. Li, Z.-Q. Lei, Y. Li, W.-H. Ye,
L.-S. Zhang, J. Sun and Z.-J. Shi, Angew. Chem., Int.
Ed., 2012, 51, 9851–9855, S9851/9851–S9851/9850;
(c) P. Kumar, K. Zhang and J. Louie, Angew. Chem., Int. Ed.,
2012, 51, 8602–8606, S8602/8601–S8602/8659; (d) C. Qin,
T. Shen, C. Tang and N. Jiao, Angew. Chem., Int. Ed., 2012,
51, 6971–6975; (e) A. Korotvicka, D. Necas and M. Kotora, 11 L. C. Morrill, T. Lebl, A. M. Z. Slawin and A. D. Smith,
Curr. Org. Chem., 2012, 16, 1170–1214; (f) W. Zhou,
Chem. Sci., 2012, 3, 2088–2093.
Y. Yang, Y. Liu and G.-J. Deng, Green Chem., 2013, 15, 12 B. List, P. Pojarliev, W. T. Biller and H. J. Martin, J. Am.
76–80; (g) C. J. Allpress, K. Grubel, E. Szajna-Fuller,
Chem. Soc., 2002, 124, 827–833.
A. M. Arif and L. M. Berreau, J. Am. Chem. Soc., 2013, 135, 13 Y. Li, Y. Meng, X. Meng and Z. Li, Tetrahedron, 2011, 67,
659–668; (h) M. Baidya and H. Yamamoto, J. Am. Chem.
4002–4008.
Soc., 2011, 133, 13880–13882; (i) C. He, S. Guo, L. Huang 14 H. Nagano, H. Ohkouchi and T. Yajima, Tetrahedron, 2003,
and A. Lei, J. Am. Chem. Soc., 2010, 132, 8273–8275;
59, 3649–3663.
( j) T. Seiser and N. Cramer, J. Am. Chem. Soc., 2010, 132, 15 (a) K. Blau, U. Kapst and V. Voerckel, J. Prakt. Chem., 1989,
5340–5341; (k) A. Sattler and G. Parkin, Nature, 2010, 463,
523–526; (l) Z. Chen, L. Wei and J. Zhang, Org. Lett., 2011,
13, 1170–1173; (m) C. Zhang, Z. Xu, T. Shen, G. Wu,
331, 671–676; (b) B. Witkop, J. Am. Chem. Soc., 1956, 78,
2873–2882; (c) M. G. Vetelino and J. W. Coe, Tetrahedron
Lett., 1994, 35, 219–222.
L. Zhang and N. Jiao, Org. Lett., 2012, 14, 2362–2365; 16 I. Ibrahem and A. Córdova, Tetrahedron Lett., 2005, 46,
(n) W. Zhou, H. Li and L. Wang, Org. Lett., 2012, 14, 4594–
4597.
3 (a) H. Liu, C. Dong, Z. Zhang, P. Wu and X. Jiang, Angew.
Chem., Int. Ed., 2012, 51, 12570–12574; (b) B. Tiwari,
2839–2843. The procedure using 4-methoxyanilinefor the
Mannich reaction as in this reference gave the corres-
ponding ester detected by mass spectra, but it has difficul-
ties in purification upon column chromatography.
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Org. Biomol. Chem., 2013, 11, 4138–4141 | 4141