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Organic & Biomolecular Chemistry
Page 5 of 6
DOI: 10.1039/C7OB00131B
Journal Name
ARTICLE
9
Selected examples: (a) M. Agostinho and S. Kobayashi, J. Am. Chem.
In conclusion, we have developed a Mg(OMe)2 promoted
allylic isomerization of γꢀhydroxyꢀα,βꢀalkenoic esters using
TMEDA as an additive. A series of γꢀketo esters were readily
Soc. 2008, 130, 2430; (b) T. Tsubogo, Y. Yamashita and S. Kobayashi,
Angew. Chem., Int. Ed. 2009, 48, 9117; (c) T. Poisson, Y. Yamashita and S.
Kobayashi, J. Am. Chem. Soc. 2010, 132, 7890.
afforded in high yield (up to 96%) under very mild conditions. 10 Selected examples: (a) D. A. Evans and S. G. Nelson, J. Am. Chem. Soc.
1997, 119, 6452; (b) T. Tsubogo, S. Saito, K. Seki, Y. Yamashita and S.
Kobayashi, J. Am. Chem. Soc. 2008, 130, 13321; (c) H. V. Nguyen, R.
Matsubara and S. Kobayashi, Angew. Chem. Int. Ed. 2009, 48, 5927.
In addition, an inꢀsitu dienolate pathway mechanism was
proposed and verified by a tandem allylic isomerizationꢀAldol
reaction, which can be applied to the synthesis of αꢀalkenylꢀγꢀ
butyrolactones. Applications and extensions of this protocol are
under investigating in our group.
11 Our recent examples: (a) L. Lin, J. Zhang, X. Ma, X. Fu and R. Wang,
Org. Lett., 2011, 13, 6410; (b) D. Yang, L. Wang, F. Han, D. Zhao, B. Zhang
and R. Wang, Angew. Chem. Int. Ed., 2013, 52, 6739; (c) D. Yang, L. Wang,
F. Han, D. Zhao and R. Wang, Chem. –Eur. J., 2014, 20, 8584; (d) D. Yang,
L. Wang, F. Han, D. Li, D. Zhao, Y. Cao, Y. Ma, W. Kong, Q. Sun and R.
Wang, Chem. –Eur. J., 2014, 20, 16478; (e) L. Wang, D. Yang, F. Han, D. Li,
D. Zhao and R. Wang, Org. Lett., 2015, 17, 176; (f) D. Yang, L. Wang, F.
Han, D. Li, D. Zhao and R. Wang, Angew. Chem. Int. Ed., 2015, 54, 2185; (g)
L. Wang, D. Yang, D. Li R. Wang, Org. Lett., 2015, 17, 3004; (h) D. Li, L.
Wang, D. Yang, B. Zhang and R. Wang, ACS Catal., 2015, 5, 7432; (i) L.
Wang, D. Li, D. Yang, K. Wang, J. Wang, P. Wang, S. Wu and R. Wang,
Chem. –Asian J., 2016, 11, 691; (j) Li, D. Wang, Y. J. Wang, L. Q. Wang, J.
Wang, P. X. Wang, K. Z. Lin, L. Liu, D. S. Jiang, X. X. Yang, D. X. Chem.
Commun., 2016, 52, 9640.
Acknowledgements
We gratefully acknowledge financial support from NSFC (nos.
21002043 and 21272107), the National S&T Major Project of
China (2012ZX09504ꢀ001ꢀ003), and the Fundamental
Research Funds for the Central Universities (2022016zr0064).
12 (a) L. Lin, X. X. Jiang, W. X. Liu, L. Qiu, Z. Q. Xu, J. K. Xu, A. S. C.
Chan and R. Wang, Org. Lett. 2007, 9, 2329; (b) L. Lin, Q. Y. Zhao, A.ꢀN.
Li, F. B. Ren, F. Z. Yang and R. Wang, Org. Biomol. Chem. 2009, 7, 3663.
13 I. K. Youn, G. H. Yon and C. S. Pak, Tetrahedron Lett. 1986, 27, 2409.
14 Aforehand prepared methanol solution of Mg(OMe)2 was used when the
reaction solvent was MeOH, otherwise solid state of Mg(OMe)2 was used.
Mg(OMe)2 was prepared following the literature : L. I. Smith and P. F.
Wiley, J. Am. Chem. Soc. 1946, 68, 887.
15 No detailed datas or subsequent report were disclosed: M. D. Giacomo, P.
Leggeri, O. Azzolina, D. Pirillo and G. Traverso, J. Chem. Res; (S) 1990, 16.
16 An excellent mechanism study by R. H. Grubbs: D. V. McGrath and R.
H. Grubbs, Organometallics 1994, 13, 224.
Notes and references
‡ Unꢀoptimized conditions.
1
Selected reviews: (a) L. A. Yanovskaya and Kh. Shakhidayatov, Russ.
Chem. Rev. 1970, 39, 859; (b) R. C. Van der Drift, E. Bowman and E. Drent,
J. Organomet. Chem. 2002, 650, 1; (c) R. Uma, C. Crévisy and R. Grée,
Chem. Rev. 2003, 103, 27; (d) V. Cadierno, P. Crochet and J. Gimeno, Synlett
2008, 8, 1105; (e) P. LorenzoꢀLuis, A. Romerosa and M. SerranoꢀRuiz, ACS
Catal. 2012, 2, 1079; (f) N. Ahlsten, A. Bartoszewicz and B. MartínꢀMatute,
Dalton Trans. 2012, 41, 1660; (g) D. Cahard, S. Gaillard and J. L. Renaud,
Tetrahedron Lett. 2015, 56, 6159; (h) H. Li and C. Mazet, Acc. Chem. Res.
2016, 49, 1232.
17 (a) Z. Lu, G. B. Chai and S. M. Ma, J. Am. Chem. Soc. 2007, 129, 14546;
(b) A. Yamaguchi, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2009, 131,
10842.
2
3
B. M. Trost, Science 1991, 254, 1471.
Selected examples: (a) B. M. Trost and R. J. Kulawiec, J. Am. Chem. Soc.
1993, 115, 2027; (b) K. Tanaka, S. Qiao, M. Tobisu, M. M.ꢀC. Lo and G. C.
Fu, J. Am. Chem. Soc. 2000, 122, 9870; (c) D. Finnegan, B. A. Seigal and M.
L. Snapper, Org. Lett. 2006, 8, 2603; (d) V. Cadierno, S. E. GarcíaꢀGarrido, J.
Gimeno, A. VarelaꢀÁlvarez and J. A. Sordo, J. Am. Chem. Soc. 2006, 128,
1360; (e) T. Doi, T. Fukuyama, S. Minamino, G. Husson and I. Ryu, Chem.
Commun. 2006, 17, 1875; (f) D. H. Leung, R. G. Bergman and K. N.
Raymond, J. Am. Chem. Soc. 2007, 129, 2746; (g) J. Petrignet, I. Prathap, S.
Chandrasekhar, J. S. Yadav and R. Grée, Angew. Chem. Int. Ed. 2007, 46,
6297; (h) B. LastraꢀBarreira, J. Díez and P. Crochet, Green Chem. 2009, 11,
1681; (i) L. Mantilli and C. Mazet, Tetrahedron Lett. 2009, 50, 4141; (j) M.
Batuecas, M. A. Esteruelas, C. GarcíaꢀYebra and E. Oňate, Organometallics
2010, 29, 2166.
18 Selected examples: (a) B. M. Trost, L. Dong and G. M. Schroeder, J. Am.
Chem. Soc. 2005, 127, 2844; (b) D. Cuperly, J. Petrignet, C. Crévisy and R.
Grée,Chem. Eur. J. 2006, 12, 3261; (c) N. Ahlstena and B. MartínꢀMatute,
Adv. Synth. Catal. 2009, 351, 2657. And references cited in.
19 It is different from the intramolecular tandem allylic isomerizationꢀAldol
reaction reported by René Grée in ref. 3g. The Reformatskyꢀlike adduct 4
was not observed while stirring 2o and benzaldehyde under standard
conditions over 24 hours.
20 B. Madrigal, P. Puebla, R. Peláez, E. Caballero and M. Medarde, J. Org.
Chem. 2003, 68, 854.
21 O. Reiser and M. Seitz, Curr. Opin. Chem. Biol. 2005, 9, 285. And
references cited in.
4
Limited catalytic systems see: (a) X. Lu, J. Ji, D. Ma and W. Shen, J.
Org. Chem. 1991, 56, 5774; (b) H. Cherkaoui, M. Soufiaoui and R. Grée,
Tetrahedron 2001, 57, 2379.
5
(a) D. R. Dimmel, W. Y. Fu and S. B. Gharpure, J. Org. Chem.1976, 41,
3092; (b) G. A. Schmid, H.ꢀJ. Borschberg, Helv.Chim. Acta. 2001, 84, 401;
(c) A. J. S. Johnston, M. G. McLaughlin, J. P. Reid and M. J. Cook, Org.
Biomol. Chem. 2013, 11, 7662; (d) H.ꢀX. Zheng, Z.ꢀF. Xiao, C.ꢀZ. Yao, Q.ꢀQ.
Li, X.ꢀS. Ning, Y.ꢀB. Kang and Y. Tang, Org. Lett. 2015, 17, 6102; (e) K.
Mondal, B. Mondal and S. C. Pan, J. Org. Chem. 2016, 81, 4835; (f) S.
MartinezꢀErro, A. SanzꢀMarco, A. B. Gómez, A. VázquezꢀRomero, M. S. G.
Ahlquist and B. MartínꢀMatute, J. Amer. Chem. Soc., 2016, 138, 13408.
6
(a) A. G. Csaky and J. Plumet, Chem. Soc. Rev. 2001, 30, 313; (b) G.
Piancatelli, M. D’Auria, F. D’Onofrio, Synthesis 1994, 867; (c) Y. S. Rao,
Chem. Rev. 1976, 76, 625; (d) L. Chen, T.ꢀD. Shi and J. Zhou, Chem. Asian
J., 2013, 8, 556–559.
7
(a) C. Nájera and M. Yust, J. Chem. Soc. Perkin. Trans. I, 1989, 8, 1387;
(b) G. M. Coppola and R. E. Damon, J. Heterocyclic Chem., 1995, 32, 1133;
(c) J. L. Shamshina and T. S. Snowden, Org. Lett. 2006, 8, 5881.
8
Recent reviews for alkalineꢀearth metal catalyzed CꢀC bond formation:
(a) U. Kazmaier, Angew. Chem., Int. Ed. 2009, 48, 5790; (b) S. Harder, Chem.
Rev. 2010, 110, 3852. And references cited in; (c) S. Kobayashi and Y.
Yamashita, Acc. Chem. Res. 2011, 44, 58.
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