Organic Letters
Letter
(
4) (a) Bode, J. W.; Fraefel, N.; Muri, D.; Carreira, E. M. Angew.
(18) (a) Hagiwara, H.; Uda, H. J. Chem. Soc., Perkin Trans. 1 1985,
1157−1159. (b) Bennett, F.; Fenton, G.; Knight, D. W. Tetrahedron
1994, 50, 5147−5158. (c) Hinterding, K.; Singhanat, S.; Oberer, L.
Tetrahedron Lett. 2001, 42, 8463−8465.
Chem., Int. Ed. 2001, 40, 2082−2085. (b) Muri, D.; Lohse-Fraefel, N.;
Carreira, E. M. Angew. Chem., Int. Ed. 2005, 44, 4036−4038.
(
(
c) Becker, N.; Carreira, E. M. Org. Lett. 2007, 9, 3857−3858.
d) Kleinbeck, F.; Carreira, E. M. Angew. Chem., Int. Ed. 2009, 48,
5
8
78−581. (e) Muri, D.; Carreira, E. M. J. Org. Chem. 2009, 74, 8695−
712.
(
5) For catalytic asymmetric syntheses of isoxazolines from nitrile
oxides, see: (a) Sibi, M.; Itoh, K.; Jasperse, C. P. J. Am. Chem. Soc.
004, 126, 5366−5367. (b) Suga, H.; Adachi, Y.; Fujimoto, K.;
Furihata, Y.; Tsuchida, T.; Kakehi, A.; Baba, T. J. Org. Chem. 2009, 74,
099−1113. (c) Lian, X.; Guo, S.; Wang, G.; Lin, L.; Liu, X.; Feng, X.
J. Org. Chem. 2014, 79, 7703−7710.
6) (a) Torssell, K. B. G.; Zeuthen, O. Acta Chem. Scand. B 1978, 32,
2
1
(
1
1
18−124. (b) Sharma, S. C.; Torssell, K. B. G. Acta Chem. Scand. B
979, 33, 379−383. (c) Torssell, K. B. G.; Hazell, A. C.; Hazell, R. G.
Tetrahedron 1985, 41, 5569−5575.
(
7) (a) Kim, B. H.; Lee, J. Y.; Kim, K.; Whang, D. Tetrahedron:
Asymmetry 1991, 2, 27−30. (b) Kim, B. H.; Lee, J. Y. Tetrahedron:
Asymmetry 1991, 2, 1359−1370. (c) Stack, J. A.; Heffner, T. A.; Geib,
S. J.; Curran, D. P. Tetrahedron 1993, 49, 995−1008. (d) Kim, B. H.;
Curran, D. P. Tetrahedron 1993, 49, 293−318. (e) Galley, G.; Jones, P.
G.; Paetzel, M. Tetrahedron: Asymmetry 1996, 7, 2073−2082.
(
f) Young, D. G. J.; Gomez-Bengoa, E.; Hoveyda, A. H. J. Org.
Chem. 1999, 64, 692−693. (g) Pitlik, J. Synth. Commun. 1994, 24,
43−252.
8) For “BINOL-Ti(IV)” catalyzed asymmetric reactions, see:
a) Mikami, K.; Matsukawa, S. Nature 1997, 385, 613−615.
b) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc.
002, 124, 10−11. (c) Yuan, Y.; Zhang, X.; Ding, K. Angew. Chem., Int.
2
(
(
(
2
Ed. 2003, 42, 5478−5480. (d) Yuan, Y.; Wang, X.; Li, X.; Ding, K. J.
Org. Chem. 2004, 69, 146−149. (e) Bao, H.; Zhou, J.; Wang, Z.; Guo,
Y.; You, T.; Ding, K. J. Am. Chem. Soc. 2008, 130, 10116−10127.
(
f) Yang, W.; Shang, D.; Liu, Y.; Du, Y.; Feng, X. J. Org. Chem. 2005,
7
2
(
0, 8533−8537. (g) He, L.; Zhao, L.; Wang, D.; Wang, M. Org. Lett.
014, 16, 5972−5975.
9) For “salen-M(III)” catalyzed asymmetric Diels−Alder reactions,
see: (a) Huang, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2000,
22, 7843−7844. (b) Kozmin, S. A.; Iwama, T.; Huang, Y.; Rawal, V.
1
H. J. Am. Chem. Soc. 2002, 124, 4628−4641. (c) Huang, Y.; Iwama, T.;
Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 5950−5951. (d) Huang, Y.;
Iwama, T.; Rawal, V. H. Org. Lett. 2002, 4, 1163−1166.
(
10) For “salen-M(III)” catalyzed asymmetric reactions, see:
a) Wang, S.; Wang, M.; Wang, D.; Zhu, J. Org. Lett. 2007, 9,
615−3618. (b) Wang, S.; Wang, M.; Wang, D.; Zhu, J. Angew. Chem.,
(
3
Int. Ed. 2008, 47, 388−391. (c) Yue, T.; Wang, M.; Wang, D.; Zhu, J.
Angew. Chem., Int. Ed. 2008, 47, 9454−9457. (d) Yang, L.; Wang, D.;
Huang, Z.; Wang, M. J. Am. Chem. Soc. 2009, 131, 10390−10391.
(
e) Tong, S.; Wang, D.; Zhao, L.; Zhu, J.; Wang, M. Angew. Chem., Int.
Ed. 2012, 51, 4417−4420.
11) For a review on chiral oxazaborolidine catalyzed reactions, see:
Corey, E. J. Angew. Chem., Int. Ed. 2009, 48, 2100−2117.
12) (a) Erkkila,
b) Erkkila, A.; Pihko, P. M. Eur. J. Org. Chem. 2007, 4205−4216.
c) Marvel, C. S.; Myers, R. L.; Saunders, J. H. J. Am. Chem. Soc. 1948,
0, 1694−1699.
13) CCDC 1046756: p-bromobenzoate of 3d; CCDC 1046755: p-
bromobenzoate of 3m.
14) (a) Vleggaar, R.; Ackerman, L. G. J.; Steyn, P. S. J. Chem. Soc.,
(
(
̈
A.; Pihko, P. M. J. Org. Chem. 2006, 71, 2538−2541.
(
(
7
̈
(
(
Perkin Trans. 1 1992, 3095−3098. (b) Bassoli, A.; Borgonovo, G.;
Busnelli, G.; Morini, G.; Drew, M. G. B. Eur. J. Org. Chem. 2005,
1
652−1658. (c) Bassoli, A.; Borgonovo, G.; Busnelli, G.; Morini, G.;
Merlini, L. Eur. J. Org. Chem. 2005, 2518−2525.
(
(
15) See Supporting Information for details.
16) For references on the syntheses of Tanikolide, see: Gourdet, B.;
Lam, H. W. Angew. Chem., Int. Ed. 2010, 49, 8733−8737 and ref 25
therein.
(
17) Curran, D. P. J. Am. Chem. Soc. 1983, 105, 5826−5833.
D
Org. Lett. XXXX, XXX, XXX−XXX