Organic Letters
Letter
D.; Lee, R.; Tong, G.; Chen, W.; Qi, B.; Huang, K.-W.; Tan, C.-H.;
Jiang, Z. Angew. Chem., Int. Ed. 2012, 51, 10069−10073. (d) Li, X.;
Lu, M.; Dong, Y.; Wu, W.; Qian, Q.; Ye, J.; Dixon, D. J. Nat. Commun.
2014, 5, 4479. (e) Yin, L.; Takada, H.; Lin, S.; Kumagai, N.;
Shibasaki, M. Angew. Chem., Int. Ed. 2014, 53, 5327−5331.
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
■
S
́
(f) Skrzynska, A.; Drelich, P.; Frankowski, S.; Albrecht, Ł. Chem. -
Eur. J. 2018, 24, 16543−16547.
Details of experimental procedures, H and 13C NMR
1
(6) (a) Cho, C.-W.; Krische, M. J. Angew. Chem., Int. Ed. 2004, 43,
6689−6691. (b) Jiang, Y.-Q.; Shi, Y.-L.; Shi, M. J. Am. Chem. Soc.
2008, 130, 7202−7203. (c) Cui, H.-L.; Huang, J.-R.; Lei, J.; Wang, Z.-
F.; Chen, S.; Wu, L.; Chen, Y.-C. Org. Lett. 2010, 12, 720−723.
(7) For selected reviews, see: (a) Trost, B. M.; Van Vranken, D. L.
Chem. Rev. 1996, 96, 395−422. (b) Helmchen, G. J. Organomet.
Chem. 1999, 576, 203−214. (c) Trost, B. M.; Crawley, M. L. Chem.
Rev. 2003, 103, 2921−2944. (d) Miyabe, H.; Takemoto, Y. Synlett
2005, 11, 1641−1655. (e) Mohr, J. T.; Stoltz, B. M. Chem. - Asian J.
2007, 2, 1476−1491. (f) Lu, Z.; Ma, S. Angew. Chem., Int. Ed. 2008,
47, 258−297. (g) Weaver, J. D.; Recio, A.; Grenning, A. J.; Tunge, J.
A. Chem. Rev. 2011, 111, 1846−1913. (h) Oliver, S.; Evans, P. A.
Synthesis 2013, 45, 3179−3198. (i) Butt, N. A.; Zhang, W. Chem. Soc.
Rev. 2015, 44, 7929−7967. (j) James, J.; Guiry, P. J. ACS Catal. 2017,
7, 1397−1402. (k) Fu, J.; Huo, X.; Li, B.; Zhang, W. Org. Biomol.
Chem. 2017, 15, 9747−9759.
spectra, HPLC chromatograms (PDF)
AUTHOR INFORMATION
■
Corresponding Author
ORCID
Author Contributions
†S.A. and T.K. contributed equally.
Notes
The authors declare no competing financial interest.
(8) (a) Fournier, J.; Arseniyadis, S.; Cossy, J. Angew. Chem., Int. Ed.
2012, 51, 7562−7566. (b) Fournier, J.; Lozano, O.; Menozzi, C.;
Arseniyadis, S.; Cossy, J. Angew. Chem., Int. Ed. 2013, 52, 1257−1261.
(c) Arseniyadis, S.; Fournier, J.; Thangavelu, S.; Lozano, O.; Prevost,
S.; Archambeau, A.; Menozzi, C.; Cossy, J. Synlett 2013, 24, 2350−
2364.
ACKNOWLEDGMENTS
Queen Mary University of London is acknowledged for
financial support.
■
REFERENCES
■
(9) Nascimento de Oliveira, M.; Fournier, J.; Arseniyadis, S.; Cossy,
(1) (a) Rao, Y. S. Chem. Rev. 1964, 64, 353−388. (b) Danishefsky,
S.; Kitahara, T.; Schuda, P. F.; Etheredge, S. J. J. Am. Chem. Soc. 1976,
98, 3028−3030. (c) Marshall, J. A.; Liao, J. J. Org. Chem. 1998, 63,
5962−5970. (d) De Souza, M. V. N. Mini-Rev. Org. Chem. 2005, 2,
139−145. (e) Robichaud, J.; Tremblay, F. Org. Lett. 2006, 8, 597−
600. (f) Boeckman, R. K.; Pero, J. E.; Boehmler, D. J. J. Am. Chem.
Soc. 2006, 128, 11032−11033. (g) Kitson, R. R. A.; Millemaggi, A.;
Taylor, R. J. K. Angew. Chem., Int. Ed. 2009, 48, 9426−9451.
(h) Lone, S. H.; Bhat, K. A.; Khuroo, M. A. Chem.-Biol. Interact. 2015,
240, 180−198.
(2) (a) Rao, Y. S. Chem. Rev. 1976, 76, 625−694. (b) Carter, N. B.;
Nadany, A. E.; Sweeney, J. B. J. Chem. Soc. Perkin 2002, 1, 2324−
2342. (c) Seitz, M.; Reiser, O. Curr. Opin. Chem. Biol. 2005, 9, 285−
292. (d) Yanai, H. Green and Catalytic Methods for γ-Lactone
Synthesis. In Green Synthetic Approaches for Biologically Relevant
Heterocycles; Brahmachari, G., Ed.; Elsevier: Boston, 2015; Chapter
J. Org. Lett. 2017, 19, 14−17.
(10) Nascimento de Oliveira, M.; Arseniyadis, S.; Cossy, J. Chem. -
Eur. J. 2018, 24, 4810−4814.
(11) Song, T.; Arseniyadis, S.; Cossy, J. Chem. - Eur. J. 2018, 24,
8076−8080.
(12) Song, T.; Arseniyadis, S.; Cossy, J. Org. Lett. 2019, 21, 603−
607.
(13) Butts, C. P.; Filali, E.; Lloyd-Jones, G. C.; Norrby, P.-O.; Sale,
D. A.; Schramm, Y. J. Am. Chem. Soc. 2009, 131, 9945−9957.
(14) (a) Ding, A.; Meazza, M.; Guo, H.; Yang, J. W.; Rios, R. Chem.
Soc. Rev. 2018, 47, 5946−5996. (b) Rios, R. Chem. Soc. Rev. 2012, 41,
1060−1074.
́
̃
anas-Mastral, M.; Feringa, B. L.
10, pp 257−289. (e) Mao, B.; Fan
Chem. Rev. 2017, 117, 10502−10566.
̀
(3) (a) Szlosek, M.; Figadere, B. Angew. Chem., Int. Ed. 2000, 39,
1799−1801. (b) Evans, D. A.; Dunn, T. B.; Kværnø, L.; Beauchemin,
A.; Raymer, B.; Olhava, E. J.; Mulder, J. A.; Juhl, M.; Kagechika, K.;
Favor, D. A. Angew. Chem., Int. Ed. 2007, 46, 4698−4703. (c) Gao, S.;
Wang, Q.; Chen, C. J. Am. Chem. Soc. 2009, 131, 1410−1412.
(d) Singh, R. P.; Foxman, B. M.; Deng, L. J. Am. Chem. Soc. 2010,
132, 9558−9560. (e) Ube, H.; Shimada, N.; Terada, M. Angew.
Chem., Int. Ed. 2010, 49, 1858−1861. (f) Luo, J.; Wang, H.; Han, X.;
Xu, L.-W.; Kwiatkowski, J.; Huang, K.-W.; Lu, Y. Angew. Chem., Int.
Ed. 2011, 50, 1861−1864. (g) Claraz, A.; Oudeyer, S.; Levacher, V.
Adv. Synth. Catal. 2013, 355, 841−846.
(4) (a) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299−
3300. (b) Martin, S. F.; Barr, K. J.; Smith, D. W.; Bur, S. K. J. Am.
Chem. Soc. 1999, 121, 6990−6997. (c) Carswell, E. L.; Snapper, M.
L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2006, 45, 7230−7233.
(d) Wieland, L. C.; Vieira, E. M.; Snapper, M. L.; Hoveyda, A. H. J.
Am. Chem. Soc. 2009, 131, 570−576. (e) Yin, L.; Takada, H.;
Kumagai, N.; Shibasaki, M. Angew. Chem., Int. Ed. 2013, 52, 7310−
7313.
(5) (a) Suga, H.; Kitamura, T.; Kakehi, A.; Baba, T. Chem. Commun.
2004, 1414−1415. (b) Simmons, B.; Walji, A. M.; MacMillan, D. W.
C. Angew. Chem., Int. Ed. 2009, 48, 4349−4353. (c) Zhang, W.; Tan,
E
Org. Lett. XXXX, XXX, XXX−XXX