Journal of the American Chemical Society
Page 8 of 9
1
2
(3) For a review, see: (a) Venkatraman, J.; Shankaramma, S. C.;
(12) For selected examples, see: (a) Han, X.; Wang, Y.; Zhong, F.;
3
4
5
6
7
8
9
Balaram, P. Chem. Rev. 2001, 101, 3131. For selected examples,
see: (b) Cativiela, C.; Díaz-De-Villegas, M. D. Tetrahedron:
Asymmetry 2007, 18, 569. (c) Cativiela, C.; Díaz-de-Villegas,
M. D. Tetrahedron: Asymmetry 1998, 9, 3517. (d) Ohfune, Y.;
Shinada, T. Eur. J. Org. Chem. 2005, 5127. (e) Tanaka, M.;
Chem. Pharm. Bull. 2007, 55, 349. (f) Vogt, H.; Bräse, S. Org.
Biomol. Chem. 2007, 5, 406.
Lu, Y. J. Am. Chem. Soc. 2011, 133, 1726. (b) Han, X.; Zhong,
F.; Wang, Y.; Lu, Y. Angew. Chem. Int. Ed. 2012, 51, 767. (c)
Zhong, F.; Han, X.; Wang, Y.; Lu, Y. Chem. Sci. 2012, 3, 1231.
(d) Zhong, F.; Han, X.; Wang, Y.; Lu, Y. Angew. Chem. Int.
Ed. 2011, 50, 7837. (e) Zhong, F.; Chen, G.-Y.; Han, X.; Yao,
W.; Lu, Y. Org. Lett. 2012, 14, 3764. (f) Han, X.; Yao, W.;
Wang, T.; Tan, Y. R.; Yan, Z.; Kwiatkowski, J.; Lu, Y. Angew.
Chem. Int. Ed. 2014, 53, 5643. (g) Han, X.; Wang, S.-X.;
Zhong, F.; Lu, Y. Synthesis 2011, 1859. (h) Yao, W.; Dou, X.;
(4) For selected examples, see: (a) Trost, B. M.; Ariza, X. J. Am.
Chem. Soc. 1999, 121, 10727. (b) Trost, B. M.; Heinemann, C.;
Ariza, X.; Weigand, S. J. Am. Chem. Soc. 1999, 121, 8667. (c)
Trost, B. M.; Dogra, K. J. Am. Chem. Soc. 2002, 124, 7256. (d)
Trost, B. M.; Jakel, C.; Plietker, B. J. Am. Chem. Soc. 2003, 125,
4438. (e) Trost, B. M.; Lara, C. C. J. Am. Chem. Soc. 2012, 134,
5778. (f) Melhado, A. D.; Luparia, M.; Toste, F. D. J. Am.
Chem. Soc. 2007, 129, 12638. (g) Weber, M.; Jautze, S.; Frey,
W.; Peters, R. J. Am. Chem. Soc. 2010, 132, 12222. (h) Chen, W.;
Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 2068.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Lu, Y. J. Am. Chem. Soc. 2015, 137, 54.
(13) For early examples, see: (a) Trost, B. M.; Li, C.-J. J. Am.
Chem. Soc. 1994, 116, 10819. (b) Trost, B. M.; Li, C.-J. J. Am.
Chem. Soc. 1994, 116, 3167. (c) Trost, B. M.; Dake, G. R. J.
Org. Chem. 1997, 62, 5670. (d) Chen, Z.; Zhu, G.; Jiang, Q.;
Xiao, D.; Cao, P.; Zhang, X. J. Org. Chem. 1998, 63, 5631. (e)
Zhang, C.; Lu, X. synlett. 1995, 645.
(14) (a) Chung, Y. K.; Fu, G. C. Angew. Chem. Int. Ed. 2009, 48,
2225. (b) Smith, S. W.; Fu, G. C. J. Am. Chem. Soc. 2009, 131,
14231. (c) Sinisi, R.; Sun, J.; Fu, G. C. Proc. Natl. Acad. Sci.
USA 2010, 107, 20652. (d) Sun, J.; Fu, G. C. J. Am. Chem. Soc.
2010, 132, 4568. (e) Fujiwara, Y.; Sun, J.; Fu, G. C. Chem. Sci.
2011, 2, 2196. (f) Lundgren, R. J.; Wilsily, A.; Marion, N.; Ma,
C.; Chung, Y. K.; Fu, G. C. Angew. Chem. Int. Ed. 2013, 52,
2525. (g) Chen, J.; Cai, Y.; Zhao, G. Adv. Synth. Catal. 2014,
356, 359. (h) Fang, Y.-Q.; Tadross, P. M.; Jacobsen, E. N. J.
Am. Chem. Soc. 2014, 136, 17966.
(5) (a) Cabrera, S.; Reyes, E.; Aleman, J.; Milelli, A.; Kobbelgaard,
S.; Jøergensen, K. A. J. Am. Chem. Soc. 2008, 130, 12031. (b)
Uraguchi, D.; Ueki, Y.; Ooi, T. Science 2009, 326, 120. (c)
Hayashi, Y.; Obi, K.; Ohta, Y.; Okamura, D.; Ishikawa, H.
Chem. Asian J. 2009, 4, 246. (d) Jiang, H.; Paixao, M. W.;
Monge, D.; Jørgensen, K. A. J. Am. Chem. Soc. 2010, 132, 2775.
(e) Alba, A.-N. R.; Valero, G.; Calbet, T.; Font-Bardía, M.; Mo-
yano, A.; Rios, R. Chem.−Eur. J. 2010, 16, 9884. (f) Alba, A.-N.
R.; Valero, G.; Calbet, T.; Font-Bardía, M.; Moyano, A.; Rios,
(15) (a) Wang, T.; Yao, W.; Zhong, F.; Pang, G. H.; Lu, Y. Angew.
Chem. Int. Ed. 2014, 53, 2964. (b) Wang, T.; Hoon, D. L.; Lu,
Y. Chem. Commun. 2015, 51, 10186. (c) Wang, T.; Yu, Z.;
Hoon, D. L.; Huang, K.-W.; Lan, Y.; Lu, Y. Chem. Sci. 2015,
6, 4912.
R. New J. Chem. 2012, 36, 613.
(6) (a) Alemán, J.; Milelli, A.; Cabrera, S.; Reyes, E.; Jørgensen, K.
A. Chem.−Eur. J. 2008, 14, 10958. (b) Balaguer, A. N.; Com-
panyo, X.; Calvet, T.; Font-Bardía, M.; Moyano, A.; Rios, R.
Eur. J. Org. Chem. 2009, 199.
(16) For an elegant report by Fu et al. on γ-additions of hetero-
cycles to γ-substituted allenoates, see: (a) Kalek, M.; Fu, G.
C. J. Am. Chem. Soc. 2015, 137, 9438. (b) Wang, D.; Wei, Y.;
Shi, M. Chem. Commun., 2012, 48, 2764. (c) Zou, Y.-Q.; Li,
C.; Rong, j.; Yan, H.; Chen, J.-R.; Xiao, W.-J. Synlett. 2011, 7,
1000.
(7) (a) Alba, A.-N. R.; Companyo, X.; Valero, G.; Moyano, A.;
Rios, R. Chem.−Eur. J. 2010, 16, 5354. (b) Bravo, N.; Alba, A.-
N. R.; Valero, G.; Companyo, X.; Moyano, A.; Rios, R. New J.
Chem. 2010, 34, 1816. (c) Liu, Q.; Qiao, B.; Chin, K. F.; Tan, C.-
H.; Jiang, Z. Adv. Synth. Catal. 2014, 356, 3777.
(8) For selected reviews, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc.
Chem. Res. 2001, 34, 535. (b) Methot, J. L.; Roush, W. R. Adv.
Synth. Catal. 2004, 346, 1035. (c) Ye, L.-W.; Zhou, J.; Tang, Y.
Chem. Soc. Rev. 2008, 37, 1140. (d) Cowen, B. J.; Miller, S. J.
Chem. Soc. Rev. 2009, 38, 3102. (e) Marinetti, A.; Voituriez, A.
Synlett 2010, 174. (f) Wang, S.-X.; Han, X.; Zhong, F.; Lu, Y.
Synlett 2011, 2766. (g) Zhao, Q.-Y.; Lian, Z.; Wei, Y.; Shi, M.
Chem. Commun. 2012, 48, 1724. (h) Wang, Z.; Xu, X.; Kwon,
O. Chem. Soc. Rev. 2014, 43, 2927. (i) Wei, Y.; Shi, M. Chem.
Asian J. 2014, 9, 2720.
(17) See the Supporting Information for details; Oxazolones
with alkyl groups at both C-2 and C-4 positions were too
unstable to be prepared.
(18) Lu, T.-J.; Lin, C.-K. J. Org. Chem. 2011, 76, 1621.
(19) (a) Xia, Y.; Liang, Y.; Chen, Y.; Wang, M.; Jiao, L.; Huang, F.;
Liu, S.; Li, Y.; Yu, Z.-X. J. Am. Chem. Soc. 2007, 129, 3470. (b)
Liang, Y.; Liu, S.; Xia, Y.; Li, Y.; Yu, Z.-X. Chem.−Eur. J. 2008,
14, 4361. (c) Liang, Y.; Liu, S.; Yu, Z.-X. Synlett 2009, 905. (d)
Dudding, T.; Kwon, O.; Mercier, E. Org. Lett. 2006, 8, 3643.
(e) Mercier, E.; Fonovic, B.; Henry, C.; Kwon, O.; Dudding,
T. Tetrahedron Lett. 2007, 48, 3617. (f) Xie, P.; Lai, W.; Geng,
Z.; Huang, Y.; Chen, R. Chem. Asian J. 2012, 7, 1533. (g) Zhao,
L.; Wen, M.; Wang, Z.-X. Eur. J. Org. Chem. 2012, 3587. (h)
Qiao, Y.; Han, K.-L. Org. Biomol. Chem. 2012, 10, 7689.
(20) See the Supporting Information for the proposed reaction
mechanism (Fig. S1) and full Gibbs free energy profiles of
the reactions (Fig. S2).
(9) For selected reviews on MBH reactions, see: (a) Basavaiah, D.;
Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447. (b)
Wei, Y.; Shi, M. Chem. Rev. 2013, 133, 6659. (c) Ma, G.-N.;
Jiang, J.-J.; Shi, M.; Wei, Y. Chem. Commun. 2009, 45, 5496.
(d) Wei, Y.; Shi, M. Acc. Chem. Res. 2010, 43, 1005. (e) Shi, Y.-
L.; Shi, M. Eur. J. Org. Chem. 2007, 2905. For our examples,
see: (f) Zhong, F.; Wang, Y.; Han, X.; Huang, K.-W.; Lu, Y.
Org. Lett. 2011, 13, 1310. (g) Han, X.; Wang, Y.; Zhong, F.; Lu,
Y. Org. Biomol. Chem. 2011, 9, 6734.
(21) For selected examples, see: (a) Green, A. G.; Liu, P.; Merlic,
C. A.; Houk, K. N. J. Am. Chem. Soc. 2014, 136, 4575. (b)
Schoenebeck, F.; Ess, D. H.; Jones, G. O.; Houk, K. N. J. Am.
Chem. Soc. 2009, 131, 8121. (c) Hayden, A. E.; Houk, K. N. J.
Am. Chem. Soc. 2009, 131, 4084. (d) Ess, D. H.; Houk, K. N. J.
Am. Chem. Soc. 2007, 129, 10646.
(10) Zhong, F.; Luo, J.; Chen, G.-Y.; Dou, X.; Lu, Y. J. Am. Chem.
Soc. 2012, 134, 10222.
(11) Zhong, F.; Dou, X.; Han, X.; Yao, W.; Zhu, Q.; Meng, Y.; Lu,
Y. Angew. Chem. Int. Ed. 2013, 52, 943.
ACS Paragon Plus Environment