The Journal of Organic Chemistry
Article
Tetrahedron 1996, 52, 3769−3826. (c) O’Byrne, A.; Murray, C.;
Keegan, D.; Palacio, C.; Evans, P.; Morgan, B. S. Org. Biomol. Chem.
2010, 8, 539−545. (d) Kumaraguru, T.; Fadnavis, N. W. Tetrahedron:
Asymmetry 2012, 23, 775−779.
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
■
S
(8) (a) Duhamel, L.; Herman, T. Tetrahedron Lett. 1985, 26, 3099−
3102. (b) Khanapure, S. P.; Najafi, N.; Manna, S.; Yang, J.-J.; Rokach,
J. J. Org. Chem. 1995, 60, 7548−7551. (c) Ogura, K.; Yamashita, M.;
Tscuhihashi, G. -i. Tetrahedron Lett. 1976, 17, 759−762. (d) Paul, K.
G.; Johnson, F.; Favara, D. J. Am. Chem. Soc. 1976, 98, 1285−1286.
Copies of 1H and 13C {1H} NMR spectra for all
compounds and HPLC/GC chromatograms of chiral
́
(e) Singh, G.; Meyer, A.; Aube, J. J. Org. Chem. 2014, 79, 452−458.
AUTHOR INFORMATION
Corresponding Authors
(Z.Z.).
(f) Ulbrich, K.; Kreitmeier, P.; Vilaivan, T.; Reiser, O. J. Org. Chem.
2013, 78, 4202−4206. (g) Leighton, J. L.; Jacobsen, E. N. J. Org. Chem.
■
́
1996, 61, 389−390. (h) Uttaro, J.-P.; Broussous, S.; Mathe, C.;
Per
(9) (a) Ahlsten, N.; Bartoszewicz, A.; Martín-Matute, B. Dalton Trans
2012, 41, 1660−1670. (b) Uma, R.; Crevisy, C.; Gree, R. Chem. Rev.
́
igaud, C. Tetrahedron 2013, 69, 2131−2136.
́
́
2003, 103, 27−51. (c) Cadierno, V.; Crochet, P.; Gimeno, J. Synlett
2008, 2008, 1105−1124. (d) van der Drift, R. C.; Bouwman, E.; Drent,
E. J. Organomet. Chem. 2002, 650, 1−24. (e) Mantilli, L.; Mazet, C.
Chem. Lett. 2011, 40, 341−344. (f) Yanovskaya, L. A.; Shakhidayatov,
K. Russ. Chem. Rev. 1970, 39, 859−874. (g) Ruthenium in Organic
Synthesis; MurahashiS.-I., Ed.; Wiley-VCH: Weinheim, 2004; pp 309−
315.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This work was financially supported by National Natural
Science Foundation of China and Science and Technology
Commission of Shanghai Municipality.
(10) For examples with Rh catalysts, see: (a) Reetz, M. T.; Guo, H.
Synlett 2006, 2006, 2127−2129. (b) Leung, D. H.; Bergman, R. G.;
Raymond, K. N. J. Am. Chem. Soc. 2007, 129, 2746−2747. (c) Tanaka,
K.; Shoji, T.; Hirano, M. Eur. J. Org. Chem. 2007, 2007, 2687−2699.
(d) Sumida, Y.; Takada, Y.; Hayashi, S.; Hirano, K.; Yorimitsu, H.;
Oshima, K. Chem. - Asian J. 2008, 3, 119−125. (e) Corkum, E. G.;
Kalapugama, S.; Hass, M. J.; Bergens, S. H. RSC Adv. 2012, 2, 3473−
3476.
REFERENCES
■
(1) (a) Dyatkina, N.; Costisella, B.; Theil, F.; von Janta-Lipinski, M.
Tetrahedron Lett. 1994, 35, 1961−1964. (b) Borthwick, A. D.;
Biggadike, k. Tetrahedron 1992, 48, 571−623. (c) Boutureira, O.;
Matheu, M. I.; Diaz, Y.; Castillon, S. Chem. Soc. Rev. 2013, 42, 5056−
5072.
(2) (a) Collins, P. W.; Djuric, S. W. Chem. Rev. 1993, 93, 1533−1564.
(b) Harre, M.; Raddatz, P.; Walenta, R.; Winterfeldt, E. Angew. Chem.,
Int. Ed. Engl. 1982, 21, 480−492. (c) Das, S.; Chandrasekhar, S.;
(11) For examples with Ru catalysts, see: (a) Martín-Matute, B.;
Bogar, K.; Edin, M.; Kaynak, F. B.; Backvall, J.-E. Chem. - Eur. J. 2005,
́
̈
11, 5832−5842. (b) Ito, M.; Kitahara, S.; Ikariya, T. J. Am. Chem. Soc.
2005, 127, 6172−6173. (c) Cadierno, V.; Francos, J.; Gimeno, J.;
Nebra, N. Chem. Commun. 2007, 2536−2538. (d) van Rijn, J. A.; Lutz,
M.; von Chrzanowski, L. S.; Spek, A. L.; Bouwman, E.; Drent, E. Adv.
Synth. Catal. 2009, 351, 1637−1647. (e) Azua, A.; Sanz, S.; Peris, E.
́
Yadav, J. S.; Gree, R. Chem. Rev. 2007, 107, 3286−3337.
(3) Mihara, H.; Sohtome, Y.; Matsunaga, S.; Shibasaki, M. Chem. -
Asian J. 2008, 3, 359−366.
́
Organometallics 2010, 29, 3661−3664. (f) García-Alvarez, J.; Gimeno,
J.; Suarez, F. J. Organometallics 2011, 30, 2893−2896. (g) Sahli, Z.;
(4) (a) Ichikawa, M.; Takahashi, M.; Aoyagi, S.; Kibayashi, C. J. Am.
Chem. Soc. 2004, 126, 16553−16558. (b) Li, F.; Castle, S. L. Org. Lett.
2007, 9, 4033−4036. (c) Kalidindi, S.; Jeong, W. B.; Schall, A.;
Bandichhor, R.; Nosse, B.; Reiser, O. Angew. Chem., Int. Ed. 2007, 46,
6361−6363. (d) Li, F.; Tartakoff, S. S.; Castle, S. L. J. Org. Chem.
2009, 74, 9082−9093. (e) Stanislawski, P. C.; Willis, A. C.; Banwell,
M. G. Chem. - Asian J. 2007, 2, 1127−1136. (f) Lu, P.; Herdtweck, E.;
Bach, T. Chem. - Asian J. 2012, 7, 1947−1958. (g) Murai, K.; Katoh, S.
-i.; Urabe, D.; Inoue, M. Chem. Sci. 2013, 4, 2364−2368.
́
Sundararaju, B.; Achard, M.; Bruneau, C. Org. Lett. 2011, 13, 3964−
3967. (h) Bizet, V.; Pannecoucke, X.; Renaud, J.-L.; Cahard, D. Adv.
Synth. Catal. 2013, 355, 1394−1402. (i) Manzini, S.; Poater, A.;
Nelson, D. J.; Cavallo, L.; Nolan, S. P. Chem. Sci. 2014, 5, 180−188.
(j) Nakamura, Y.; Ohta, T.; Oe, Y. Chem. Commun. 2015, 51, 7459−
7462.
(12) For examples with Ir catalysts, see: (a) Mantilli, L.; Mazet, C.
Chimia 2009, 63, 35−37. (b) Vazquez-Romero, A.; Gomez, A. B.;
́ ́
(5) (a) Theil, F.; Schick, H.; Winter, G.; Reck, G. Tetrahedron 1991,
47, 7569−7582. (b) Theil, F.; Ballschuh, S.; Schick, H.; Haupt, M.;
Hafner, B.; Schwarz, S. Synthesis 1988, 1988, 540−541. (c) Johnson, C.
R.; Bis, S. J. Tetrahedron Lett. 1992, 33, 7287−7290. (d) Johnson, C.
R.; Nerurkar, B. M.; Golebiowski, A.; Sundram, H.; Esker, J. L. J. Chem.
Soc., Chem. Commun. 1995, 1139−1140.
Martín-Matute, B. ACS Catal. 2015, 5, 708−714. (c) Nelson, D. J.;
Fernandez-Salas, J. A.; Truscott, B. J.; Nolan, S. P. Org. Biomol. Chem.
2014, 12, 6672−6676. (d) Ahlsten, N.; Bermejo Gomez, A.; Martín-
Matute, B. Angew. Chem., Int. Ed. 2013, 52, 6273−6276. (e) Li, H.;
Achard, M.; Bruneau, C.; Sortais, J.-B.; Darcel, C. RSC Adv. 2014, 4,
25892−25897. (f) Li, H.; Mazet, C. J. Am. Chem. Soc. 2015, 137,
10720−10727.
̈
(6) (a) Laumen, K.; Schneider, M. Tetrahedron Lett. 1984, 25, 5875−
5878. (b) Nara, M.; Terashima, S.; Yamada, S. Tetrahedron 1980, 36,
3161−3170. (c) Gais, H.-J.; Bondarev, O.; Hetzer, R. Tetrahedron Lett.
2005, 46, 6279−6283. (d) Paquette, L. A.; Earle, M. J.; Smith, G. F.
Org. Synth. 1996, 73, 36−43. (e) Paquette, L. A.; Heidelbaugh, T. M.
Org. Synth. 1996, 73, 44−50. (f) Sugai, T.; Mori, K. Synthesis 1988,
1988, 19−22. (g) Wang, Y. F.; Chen, C. S.; Girdaukas, G.; Sih, C. J. J.
Am. Chem. Soc. 1984, 106, 3695−3696. (h) Kalkote, U. R.; Ghorpade,
S. R.; Joshi, R. R.; Ravindranathan, T.; Bastawade, K. B.; Gokhale, D.
V. Tetrahedron: Asymmetry 2000, 11, 2965−2970. (i) Deardorff, D. R.;
Amador, R. B.; Morton, J. W.; Kim, H. Y.; Taniguchi, C. M.; Balbuena,
A. A.; Warren, S. A.; Fanous, V.; Choe, S. W. T. Tetrahedron:
Asymmetry 1999, 10, 2139−2152. (j) Deardorff, D. R.; Windham, C.
Q.; Craney, C. L. Org. Synth., Coll. Vol. IX 1998, 487−492.
(13) For examples with Ni catalysts, see: (a) Bricout, H.; Monflier,
E.; Carpentier, J.-F.; Mortreux, A. Eur. J. Inorg. Chem. 1998, 1998,
1739−1744. (b) Cuperly, D.; Petrignet, J.; Crev
- Eur. J. 2006, 12, 3261−3274.
(14) For examples with Fe catalysts, see: (a) Cherkaoui, H.;
Soufiaoui, M.; Gree, R. Tetrahedron 2001, 57, 2379−2383. (b) Crevisy,
C.; Wietrich, M.; Le Boulaire, V.; Uma, R.; Gree, R. Tetrahedron Lett.
2001, 42, 395−398. (c) Branchadell, V.; Crevisy, C.; Gree, R. Chem. -
Eur. J. 2003, 9, 2062−2067.
́ ́
isy, C.; Gree, R. Chem.
́
́
́
́
́
(15) (a) Tanaka, K.; Qiao, S.; Tobisu, M.; Lo, M. M. -C.; Fu, G. C. J.
Am. Chem. Soc. 2000, 122, 9870−9871. (b) Li, J.-Q.; Peters, B.;
Andersson, P. G. Chem. - Eur. J. 2011, 17, 11143−11145. (c) Wu, R.;
Beauchamps, M. G.; Laquidara, J. M.; Sowa, J. R., Jr Angew. Chem., Int.
(7) (a) Myers, A. G.; Hammond, M.; Wu, Y. Tetrahedron Lett. 1996,
37, 3083−3086. (b) Schoffers, E.; Golebiowski, A.; Johnson, C. R.
́
Ed. 2012, 51, 2106−2110. (d) Mantilli, L.; Gerard, D.; Torche, S.;
12578
J. Org. Chem. 2015, 80, 12572−12579