Organic Letters
Letter
Brodbeck, R.; Kieltyka, A.; Hoffman, D.; Bacolod, M. D.; Girard, B.;
Tran, J.; Thurkauf, A. J. Med. Chem. 2000, 43, 3923. (f) Mohapatra, D.
K.; Datta, A. J. Org. Chem. 1998, 63, 642.
(13) Conversion of 1 (X = O-t-Bu) and 3q to diol provided same
product, and (−)-hamavellone B was synthesized with ent-2f catalyst;
(2) Selected reviews: (a) Bartoli, G.; Bencivenni, G.; Dalpozzo, R.
Synthesis 2014, 46, 979. (b) Lebel, H.; Marcoux, J.-F.; Molinaro, C.;
Charette, A. B. Chem. Rev. 2003, 103, 977. (c) Pellissier, H.
Tetrahedron 2008, 64, 7041.
(3) For selected examples of transition-metal-catalyzed asymmetric
cyclopropanation, see: (a) Zhu, S.; Perman, J. A.; Zhang, X. P. Angew.
Chem., Int. Ed. 2008, 47, 8460. (b) Fantauzzi, S.; Gallo, E.; Rose, E.;
Raoul, N.; Caselli, A.; Issa, S.; Ragaini, F.; Cenini, S. Organometallics
̈
2008, 27, 6143. (c) Ozuduru, G.; Schubach, T.; Boysen, M. M. K. Org.
̈
Lett. 2012, 14, 4990. (d) Lindsay, V. N. G.; Lin, W.; Charette, A. B. J.
Am. Chem. Soc. 2009, 131, 16383. (e) Lindsay, V. N. G.; Fiset, D.;
Gritsch, P. J.; Azzi, S.; Charette, A. B. J. Am. Chem. Soc. 2013, 135,
1463. (f) Qin, C.; Boyarskikh, V.; Hansen, J. H.; Hardcastle, K. I.;
Musaev, D. G.; Davies, H. M. L. J. Am. Chem. Soc. 2011, 133, 19198.
(g) Ito, J.-i.; Ujiie, S.; Nishiyama, H. Chem. - Eur. J. 2010, 16, 4986.
(h) Suematsu, H.; Kanchiku, S.; Uchida, T.; Katsuki, T. J. Am. Chem.
Soc. 2008, 130, 10327.
(4) For selected examples of MIRC reaction using diazo compounds,
see: (a) Doyle, M. P.; Buhro, W. E.; Dellaria, J. F., Jr. Tetrahedron Lett.
1979, 20, 4429. (b) Branstetter, B.; Hossain, M. M. Tetrahedron Lett.
2006, 47, 221. (c) Hashimoto, T.; Naganawa, Y.; Kano, T.; Maruoka,
K. Chem. Commun. 2007, 5143. (d) Gao, L.; Hwang, G.-S.; Ryu, D. H.
J. Am. Chem. Soc. 2011, 133, 20708.
(5) (a) Trost, B. M.; Dirat, O.; Gunzner, J. L. Angew. Chem., Int. Ed.
2002, 41, 841. (b) Zhang, M.-X.; Eaton, P. E. Angew. Chem., Int. Ed.
2002, 41, 2169. (c) Miller, J. A.; Hennessy, E. J.; Marshall, W. J.;
Scialdone, M. A.; Nguyen, S. T. J. Org. Chem. 2003, 68, 7884.
(d) Sørensen, U. S.; Bleisch, T. J.; Kingston, A. E.; Wright, R. A.;
Johnson, B. G.; Schoepp, D. D.; Ornstein, P. L. Bioorg. Med. Chem.
2003, 11, 197. (e) Pokorski, J. K.; Myers, M. C.; Appella, D. H.
Tetrahedron Lett. 2005, 46, 915.
(6) Successful applications of α-alkyl-α-diazoesters have been
recently realized in Rh(II)-catalyzed reactions; see: (a) Goto, T.;
Takeda, K.; Anada, M.; Ando, K.; Hashimoto, S. Tetrahedron Lett.
2011, 52, 4200. (b) DeAngelis, A.; Dmitrenko, O.; Yap, G. P. A.; Fox,
J. M. J. Am. Chem. Soc. 2009, 131, 7230. (c) Panne, P.; DeAngelis, A.;
Fox, J. M. Org. Lett. 2008, 10, 2987.
(7) Isaka, M.; Chinthanom, P.; Veeranondha, S.; Supothina, S.;
Luangsa-ard, J. J. Tetrahedron 2008, 64, 11028.
(8) The trans geometry means the ester and aldehyde groups are
directed trans to each other in the cyclopropane.
(9) (a) Lee, S. I.; Kang, B. C.; Hwang, G.-S.; Ryu, D. H. Org. Lett.
2013, 15, 1428. (b) Lee, S. I.; Hwang, G.-S.; Ryu, D. H. J. Am. Chem.
Soc. 2013, 135, 7126.
(10) (a) Gao, L.; Hwang, G.-S.; Lee, M. Y.; Ryu, D. H. Chem.
Commun. 2009, 5460. (b) Lee, S. I.; Kim, K. E.; Hwang, G.-S.; Ryu, D.
H. Org. Biomol. Chem. 2015, 13, 2745. (c) Sibi, M. P.; Stanley, L. M.;
Soeta, T. Org. Lett. 2007, 9, 1553. (d) Kano, T.; Hashimoto, T.;
Maruoka, K. J. Am. Chem. Soc. 2006, 128, 2174.
(11) (a) Gao, L.; Kang, B. C.; Hwang, G.-S.; Ryu, D. H. Angew.
Chem., Int. Ed. 2012, 51, 8322. (b) Kang, B. C.; Nam, D. G.; Hwang,
G.-S.; Ryu, D. H. Org. Lett. 2015, 17, 4810. (c) Shin, S. H.; Baek, E. H.;
Hwang, G.-S.; Ryu, D. H. Org. Lett. 2015, 17, 4746. (d) Li, W.; Wang,
J.; Hu, X.; Shen, K.; Wang, W.; Chu, Y.; Lin, L.; Liu, X.; Feng, X. J. Am.
Chem. Soc. 2010, 132, 8532.
(12) For the synthetic application of halocyclopropanes, see:
(a) Hohn, E.; Pietruszka, J. Adv. Synth. Catal. 2004, 346, 863.
(b) Beaulieu, L.-P. B.; Zimmer, L. E.; Gagnon, A.; Charette, A. B.
Chem. - Eur. J. 2012, 18, 14784. (c) Baird, M. S.; Fitton, H. L.; Clegg,
W.; McCamley, A. J. Chem. Soc., Perkin Trans. 1 1993, 321.
(d) Sheshenev, A. E.; Baird, M. S.; Croft, A. K.; Starikova, Z. A.;
Shashkov, A. S.; Zhuze, A. L.; Bolesov, I. G. Tetrahedron Lett. 2006, 47,
2839. (e) Tverezovsky, V. V.; Baird, M. S.; Bolesov, I. G. Tetrahedron
1997, 53, 14773.
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