The Journal of Organic Chemistry
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Prior reports on the B/Zn exchange and application in stereoselective reactions: (a) Srebnik, M.
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Tetrahedron Lett. 1991, 32, 2449ꢀ2452. (b) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170ꢀ
173. (c) Oppolzer, W.; Radinov, R. N. J. Am. Chem. Soc. 1993, 115, 1593ꢀ1594. (d) Langer, F.; Schwink,
L.; Devasagayaraj, A.; Chavant, P. ꢀY.; Knochel, P. J. Org. Chem. 1996, 61, 8229ꢀ8243. (e) Boudier, A.;
Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem. Int. Ed. 2000, 39, 4414ꢀ4435.
5 Martins, B. S.; Lüdtke, D. S. Eur. J. Org. Chem. 2014, 5364ꢀ5369.
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6 For additional examples on the chelationꢀcontrolled diastereoselective additon of organozinc reagents to
αꢀoxygenated aldehydes and ketones, see: (a) Stanton, G. R.; Johnson, C. N.; Walsh, P. J. J. Am. Chem.
Soc. 2010, 132, 4399ꢀ4408. (b) Stanton, G. R.; Walsh, P. J. J. Am. Chem. Soc. 2011, 133, 7969ꢀ7976.
7 Bejjani, J.; Chemla, F.; Audouin, M. J. Org. Chem. 2003, 68, 9747ꢀ9752.
8 Review: Karjalainen, O. K.; Koskinen, A. M. P. Org. Biomol. Chem. 2012, 10, 4311ꢀ4326.
9 Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem. Int. Ed. Engl. 1987, 26, 1141ꢀ1143.
10 Review: Reetz, M. T. Chem. Rev. 1999, 99, 1121ꢀ1162.
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(a) Nicholas, G. M.; Molinski, T. F. J. Am. Chem. Soc. 2000, 122, 4011ꢀ4019. (b) Andrés; J. M.; Barrio,
R.; Martínez, M. A.; Pedrosa, R.; PérezꢀEncabo, A. J. Org. Chem. 1996, 61, 4210ꢀ4213.
12 Barbie, P.; Kazmaier, U. Org. Lett. 2016, 18, 204ꢀ207.
13 Husain, A.; Ganem, B. Tetrahedron Lett. 2002, 43, 8621ꢀ8623.
14 Drewes, M. W.; Ph.D. Thesis, PhilippsꢀUniversität Marburg, Germany, 1988.
15 For selected examples, see: (a) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc.
1997, 119, 656ꢀ673. (b) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L.
J. Am. Chem. Soc. 1997, 119, 6496ꢀ6511. (c) Morales, M. R.; Mellem, K. T.; Myers, A. G. Angew. Chem.
Int. Ed. 2012, 51, 4568ꢀ4571. (d) Medley, J. W.; Movassaghi, M. Angew. Chem. Int. Ed. 2012, 51, 4572ꢀ
4576. (e) Mellen, K. T.; Myers, A. G. Org. Lett. 2013, 15, 5594ꢀ5597. (f) Hugelshofer, C. L.; Mellen, K. T.;
Myers, A. G. Org. Lett. 2013, 15, 3134ꢀ3137.
16 (a) Seiple, I. B.; Mercer, J. A. M.; Sussman, R. J.; Zhang, Z.; Myers, A. G. Angew. Chem. Int. Ed. 2014,
53, 4642ꢀ4647. (b) Seiple, I. B.; Zhang, Z.; Jakubec, P.; LangloisꢀMercier, A.; Wright, P. M.; Hog, D. T.;
Yabu, K.; Allu, S. R.; Fukuzaki, T.; Carlsen, P. N.; Kitamura, Y.; Zhou, X.; Condakes, M. L.; Szczypiński,
F. T.; Green, W. D.; Myers, A. G. Nature 2016, 533, 338ꢀ345.
17 Peng, B.; Geerdink, D.; Maulide, N. J. Am. Chem. Soc. 2013, 135, 14968ꢀ14971.
18 Atkinson, R. C.; FernándezꢀNieto, F.; Roselló, J. M.; Clayden, J. Angew. Chem. Int. Ed. 2015, 54, 8961ꢀ
8965.
19 Enders, D.; Zhu, J.; Raabe, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 1725ꢀ1728.
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Chen, S.; Fahmi, N. E.; Wang, L.; Bhattacharya, C.; Benkovic, S. J.; Hecht, S. M. J. Am. Chem. Soc.
2013, 135, 12924ꢀ12927.
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(a) Bredholt, T.; Ersvaer, E.; Erikstein, B. S.; Sulen, A.; Reikvam, H.; Aarstad, H. J.; Johannessen, A.
C.; Vintermyr, O. K.; Bruserud, O.; Gjertsen, B. T. BMC Pharmacol. Toxicol. 2013, 14, 35. (b) Nichols, T.;
Khondkar, P.; Gibbons, S. Phytochem. Lett. 2015, 13, 127ꢀ133. (c) Getasetegn, M. Phytochem. Rev.
2016, 15, 907ꢀ920.
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The NꢀNꢀdibenzylamino aldehydes were prepared according to Reetz protocol: Reetz, M. T.; Drewes,
M. W.; Schwickardi, R. Org. Synth. 1999, 76, 110.
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