Organic Letters
Letter
Allied Project (CAP)], and the Korea Basic Science Institute
[C35705].
REFERENCES
■
(
1) Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH:
Weinheim, 2004.
2) For reviews, see: (a) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917.
(
(
b) Trost, B. M.; Brindle, C. S. Chem. Soc. Rev. 2010, 39, 1600.
(
c) Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007,
1
(
07, 5471. (d) Mlynarski, J.; Bas,
3) For stoichiometric asymmetric methods, see: (a) Russell, M. G.
́
S. Chem. Soc. Rev. 2014, 43, 577.
N.; Baker, R.; Castro, J. L. Tetrahedron Lett. 1999, 40, 8667. (b) Baker,
R.; Cooke, N. G.; Humphrey, G. R.; Wright, S. H. B.; Hirshfield, J. J.
Chem. Soc., Chem. Commun. 1987, 1102. (c) Okazaki, M.; Shuto, Y.
Biosci., Biotechnol., Biochem. 2001, 65, 1134. (d) Churcher, I.; Williams,
S.; Kerrad, S.; Harrison, T.; Castro, J. L.; Shearman, M. S.; Lewis, H.
D.; Clarke, E. E.; Wrigley, J. D. J.; Beher, D.; Tang, Y. S.; Liu, W. J.
Med. Chem. 2003, 46, 2275. (e) Ahn, M.; Tanaka, K.; Fuji, K. J. Chem.
Soc., Perkin Trans. 1 1998, 185. (f) Fringuelli, F.; Piermatti, O.; Pizzo,
F. J. Org. Chem. 1995, 60, 7006. For catalytic asymmetric methods,
see: (g) Rossi, S.; Benaglia, M.; Cozzi, F.; Genoni, A.; Benincori, T.
Adv. Synth. Catal. 2011, 353, 848. (h) Wang, H.; Li, G.; Engle, K. M.;
Yu, J.-Q.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 6774.
(
1
i) Davies, H. M. L.; Hedley, S. J.; Bohall, B. R. J. Org. Chem. 2005, 70,
0737.
4) (a) 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. (b) Gao, L.; Kang,
B. C.; Hwang, G.-S.; Ryu, D. H. Angew. Chem., Int. Ed. 2012, 51, 8322.
For related regioselective examples, see: (c) Gao, L.; Kang, B. C.; Ryu,
D. H. J. Am. Chem. Soc. 2013, 135, 14556. (d) Hashimoto, T.;
Naganawa, Y.; Maruoka, K. J. Am. Chem. Soc. 2008, 130, 2434.
(
5) (a) Corey, E. J. Angew. Chem., Int. Ed. 2009, 48, 2100.
(
b) Senapati, B. K.; Hwang, G.-S.; Lee, S.; Ryu, D. H. Angew. Chem.,
Int. Ed. 2009, 48, 4398. (c) Senapati, B. K.; Gao, L.; Lee, S. I.; Hwang,
G.-S.; Ryu, D. H. Org. Lett. 2010, 12, 5088. (d) Lee, S. I.; Kang, B. C.;
Hwang, G.-S.; Ryu, D. H. Org. Lett. 2013, 15, 1428. (e) Lee, S. I.;
Hwang, G.-S.; Ryu, D. H. J. Am. Chem. Soc. 2013, 135, 7126.
(
6) Asymmetric Roskamp reaction between piperidine α-phenyl
diazoamide and p-tolualdehyde provided 1,2-hydride shift product 1 as
a major product in ∼ 50% yield with a 1/3 ratio of 6/1. For the
diastereocontrol effect of diazoamide, see: Marcoux, D.; Goudreau, S.
R.; Charette, A. B. J. Org. Chem. 2009, 74, 8939.
(
7) (a) Mentzel, M.; Hoffmann, H. M. R. J. Prakt. Chem./Chem.-Ztg.
8) Gensler, W. J.; Johnson, F.; Sloan, D. B. J. Am. Chem. Soc. 1960,
2, 6074.
9) Jiao, X.; Wang, L.; Xiao, Q.; Xie, P.; Liang, X. J. Asian Nat. Prod.
Res. 2009, 11, 274.
10) (a) Kang, B. C.; Shim, S. Y.; Ryu, D. H. Org. Lett. 2014, 16,
077. (b) Mahrwald, R.; Schetter, B. Org. Lett. 2006, 8, 281.
c) Schetter, B.; Ziemer, B.; Schnakenburg, G.; Mahrwald, R. J. Org.
Chem. 2008, 73, 813.
11) Maggiotti, V.; Wong, J.-B.; Razet, R.; Cowley, A. R.;
Gouverneur, V. Tetrahedron: Asymmetry 2002, 13, 1789.
1
(
8
(
(
2
(
(
(
(
12) Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 5384.
13) For selected reviews on π−π interaction, see: (a) Waters, M. L.
Curr. Opin. Chem. Biol. 2002, 6, 736. (b) Hunter, C. A.; Lawson, K. R.;
Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2 2001, 651.
(
2
(
c) Salonen, L. M.; Ellermann, M.; Diederich, F. Angew. Chem., Int. Ed.
011, 50, 4808. For selected paper on π−π interaction, see:
d) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525.
14) Oishi, T.; Nakata, T. Acc. Chem. Res. 1984, 17, 338.
(
D
Org. Lett. XXXX, XXX, XXX−XXX