Communication
Organic & Biomolecular Chemistry
and high enantioselectivities. The reaction is amenable to the
gram scale. The resulting 5-bromo-1,3-oxazinan-2-one can be
further transformed into various useful compounds contain-
ing diverse functional groups. Further efforts will be devoted
to understanding the reaction mechanism and the effect of
additives, developing more efficient catalytic systems, and
expanding the substrate scope.
4 For leading references on chiral base catalyzed intramole-
cular enantioselective halogenation of olefins, see:
(a) M. Wang, L. X. Gao, W. P. Mai, A. X. Xia, F. Wang and
S. B. Zhang, J. Org. Chem., 2004, 69, 2874; (b) A. Sakakura,
A. Ukai and K. Ishihara, Nature, 2007, 445, 900;
(c) D. C. Whitehead, R. Yousefi, A. Jaganathan and
B. Borhan, J. Am. Chem. Soc., 2010, 132, 3298; (d) W. Zhang,
S. Zheng, N. Liu, J. B. Werness, I. A. Guzei and W. Tang,
J. Am. Chem. Soc., 2010, 132, 3664; (e) G. E. Veitch and
E. N. Jacobsen, Angew. Chem., Int. Ed., 2010, 49, 7332;
Acknowledgements
(
f) K. Murai, T. Matsushit, A. Nakamura, S. Fukushima,
We gratefully acknowledge the National Basic Research
Program of China (973 program, 2011CB808600), the National
Natural Science Foundation of China (21172221), and the
Chinese Academy of Sciences for financial support.
M. Shimura and H. Fujioka, Angew. Chem., Int. Ed., 2010,
49, 9174; (g) L. Zhou, C. K. Tan, X. Jiang, F. Chen and
Y.-Y. Yeung, J. Am. Chem. Soc., 2010, 132, 15474;
(h) R. Yousefi, D. C. Whitehead, J. M. Mueller, R. J. Staples
and B. Borhan, Org. Lett., 2011, 13, 608; (i) N. Liu,
J. B. Werness, I. A. Guzei and W. Tang, Tetrahedron, 2011,
6
7, 4385; ( j) C. K. Tan, L. Zhou and Y.-Y. Yeung, Org. Lett.,
Notes and references
2011, 13, 2738; (k) A. Jaganathan, A. Garzan,
1
For leading reviews on asymmetric halogenation of olefins,
see: (a) G. Chen and S. Ma, Angew. Chem., Int. Ed., 2010, 49,
D. C. Whitehead, R. J. Staples and B. Borhan, Angew.
Chem., Int. Ed., 2011, 50, 2593; (l) O. Lozano, G. Blessley,
T. M. Campo, A. L. Thompson, G. T. Giuffredi, M. Bettati,
M. Walker, R. Borman and V. Gouverneur, Angew. Chem.,
Int. Ed., 2011, 50, 8105; (m) Z.-M. Chen, Q.-W. Zhang,
Z.-H. Chen, H. Li, Y.-Q. Tu, F.-M. Zhang and J.-M. Tian, J.
Am. Chem. Soc., 2011, 133, 8818; (n) L. Zhou, J. Chen,
C. K. Tan and Y.-Y. Yeung, J. Am. Chem. Soc., 2011, 133,
9164; (o) C. H. Müller, M. Wilking, A. Rühlmann,
B. Wibbeling and U. Hennecke, Synlett, 2011, 2043;
(p) J. Chen, L. Zhou, C. K. Tan and Y.-Y. Yueng, J. Org.
Chem., 2012, 77, 999; (q) W. Zhang, N. Liu,
C. M. Schienebeck, K. Decloux, S. Zheng, J. B. Werness and
W. Tang, Chem. – Eur. J., 2012, 18, 7296; (r) J. Chen,
L. Zhou and Y.-Y. Yeung, Org. Biomol. Chem., 2012, 10,
3808; (s) X. Jiang, C. K. Tan, L. Zhou and Y.-Y. Yeung,
Angew. Chem., Int. Ed., 2012, 51, 7771; (t) M. C. Dobish and
J. N. Johnston, J. Am. Chem. Soc., 2012, 134, 6068;
(u) D. H. Paull, C. Fang, J. R. Donald, A. D. Pansick and
S. F. Martin, J. Am. Chem. Soc., 2012, 134, 11128;
(v) J. E. Tungen, J. M. J. Nolsøe and T. V. Hansen, Org. Lett.,
2012, 14, 5884; (w) K. Ikeuchi, S. Ido, S. Yoshimura,
T. Asakawa, M. Inai, Y. Hamashima and T. Kan, Org. Lett.,
2012, 14, 6016; (x) X. Zeng, C. Miao, S. Wang, C. Xia and
W. Sun, Chem. Commun., 2013, 49, 2418; (y) F. Chen,
C. K. Tan and Y.-Y. Yeung, J. Am. Chem. Soc., 2013, 135,
1232; (z) M. Wilking, C. Mück-Lichtenfeld, C. G. Daniliuc
and U. Hennecke, J. Am. Chem. Soc., 2013, 135, 8133;
(aa) R. Yousefi, K. D. Ashtekar, D. C. Whitehead,
J. E. Jackson and B. Borhan, J. Am. Chem. Soc., 2013, 135,
14524; (ab) A. Jaganathan, R. J. Staples and B. Borhan,
J. Am. Chem. Soc., 2013, 135, 14806; (ac) A. Armstrong,
D. C. Braddock, A. X. Jones and S. Clark, Tetrahedron Lett.,
2013, 54, 7004; (ad) Y. Zhao, X. Jiang and Y.-Y. Yeung,
Angew. Chem., Int. Ed., 2013, 52, 8597; (ae) L. Zhou,
D. W. Tay, J. Chen, G. Y. C. Leung and Y.-Y. Yeung, Chem.
Commun., 2013, 49, 4412; (af) K. Murai, T. Matsushita,
8
2
306; (b) A. Castellanos and S. P. Fletcher, Chem. – Eur. J.,
011, 17, 5766; (c) C. K. Tan, L. Zhou and Y.-Y. Yeung,
Synlett, 2011, 1335; (d) U. Hennecke, Chem. – Asian J., 2012,
, 456; (e) S. E. Denmark, W. E. Kuester and M. T. Burk,
7
Angew. Chem., Int. Ed., 2012, 51, 10938; (f) K. Murai and
H. Fujioka, Heterocycles, 2013, 87, 763; (g) S. R. Chemler
and M. T. Bovino, ACS Catal., 2013, 3, 1076; (h) C. K. Tan
and Y.-Y. Yeung, Chem. Commun., 2013, 49, 7985;
(
i) Y. A. Cheng, W. Z. Yu and Y.-Y. Yeung, Org. Biomol.
Chem., 2014, 12, 2333; ( j) J. Chen and L. Zhou, Synthesis,
014, 46, 586; (k) S. Zheng, C. M. Schienebeck, W. Zhang,
2
H.-Y. Wang and W. Tang, Asian J. Org. Chem., 2014, 3, 366.
For leading references on Lewis acid-catalyzed intramolecu-
lar enantioselective halogenation of olefins, see:
2
3
(
a) T. Inoue, O. Kitagawa, O. Ochiai, M. Shiro and
T. Taguchi, Tetrahedron Lett., 1995, 36, 9333; (b) S. H. Kang,
S. B. Lee and C. M. Park, J. Am. Chem. Soc., 2003, 125,
1
5748; (c) Z. Ning, R. Jin, J. Ding and L. Gao, Synlett, 2009,
2
291.
For leading references on chiral phosphoric acid and phos-
phate catalyzed intramolecular enantioselective halogena-
tion of olefins, see: (a) U. Hennecke, C. H. Müller and
R. Fröhlich, Org. Lett., 2011, 13, 860; (b) D. Huang,
H. Wang, F. Xue, H. Guan, L. Li, X. Peng and Y. Shi, Org.
Lett., 2011, 13, 6350; (c) V. Rauniyar, A. D. Lackner,
G. L. Hamilton and F. D. Toste, Science, 2011, 334, 1681;
(
(
d) S. E. Denmark and M. T. Burk, Org. Lett., 2012, 14, 256;
e) Y.-M. Wang, J. Wu, C. Hoong, V. Rauniyar and
F. D. Toste, J. Am. Chem. Soc., 2012, 134, 12928;
f) F. Romanov-Michailidis, L. Guénée and A. Alexakis,
(
Angew. Chem., Int. Ed., 2013, 52, 9266; (g) W. Xie, G. Jiang,
H. Liu, J. Hu, X. Pan, H. Zhang, X. Wan, Y. Lai and D. Ma,
Angew. Chem., Int. Ed., 2013, 52, 12924; (h) H. Liu, G. Jiang,
X. Pan, X. Wan, Y. Lai, D. Ma and W. Xie, Org. Lett., 2014,
1
6, 1908.
Org. Biomol. Chem.
This journal is © The Royal Society of Chemistry 2015