Journal of the American Chemical Society
Communication
(14) For directed approaches, see: (a) Ohmura, T.; Awano, T.;
Suginome, M. J. Am. Chem. Soc. 2010, 132, 13191−13193. (b) Awano,
T.; Ohmura, T.; Suginome, M. J. Am. Chem. Soc. 2011, 133, 20738−
20741. (c) Lee, J. C. H.; MacDonald, R.; Hall, D. G. Nat. Chem. 2011,
3, 894−899. (d) Sandrock, D. L.; Jean-Gerard, L.; Chen, C.-Y.; Dreher,
S. D.; Molander, G. A. J. Am. Chem. Soc. 2010, 132, 17108−17110.
(15) Glasspoole, B. W.; Oderinde, M. S.; Moore, B. D.; Antoft-Finch,
A.; Crudden, C. M. Synthesis 2013, 1759.
chemistry. This material is available free of charge via the
AUTHOR INFORMATION
Corresponding Author
■
Notes
(16) Matteson, D. S. Tetrahedron 1998, 54, 10555−10606.
(17) (a) Bagutski, V.; French, R. M.; Aggarwal, V. K. Angew. Chem.,
Int. Ed. 2010, 49, 5142−5145. (b) Stymiest, J. L.; Bagutski, V.; French,
R. M.; Aggarwal, V. K. Nature 2008, 456, 778−782.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
(18) Alkyl 2,4,6-triisopropylbenzoates did not prove helpful in this
case: Larouche-Gauthier, R.; Fletcher, C. J.; Couto, I.; Aggarwal, V. K.
Chem. Commun. 2011, 47, 12592−12594.
C.M.C. acknowledges the Natural Sciences and Engineering
Research Council of Canada (NSERC) and the Canada
Foundation for Innovation (CFI) for support. B.W.G. thanks
NSERC for a postgraduate scholarship and Queen’s University
for Queen’s Graduate Awards. Prof. Elizabeth Jarvo from the
University of California, Irvine, is thanked for providing an
authentic compound for analysis by HPLC, and Prof. P.
Andrew Evans and his group are thanked for their assistance
with HPLC separations. B.C. is thanked for assistance with this
manuscript.
(19) (a) Lange, H.; Huenerbein, R.; Frohlich, R.; Grimme, S.;
Hoppe, D. Chem.Asian J. 2008, 3, 78−87. (b) Lange, H.;
Huenerbein, R.; Wibbeling, B.; Frohlich, R.; Grimme, S.; Hoppe, D.
̈
Synthesis 2008, 2905−2918.
(20) For the use of neopentyl boronic esters in order to prepare
unhindered allylic boronic esters, see: Aggarwal, V. K.; Althaus, M.;
Mahmood, A.; Suarez, J. R.; Thomas, S. P. J. Am. Chem. Soc. 2010, 132,
4025−4028.
(21) es = (%ee product/%ee starting material) × 100%
REFERENCES
■
(1) Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111,
1417−1492.
(2) Greene, M. A.; Yonova, I. M.; Williams, F. J.; Jarvo, E. R. Org.
Lett. 2012, 14, 4293−4296.
(3) (a) Parai, M. K.; Panda, G.; Chaturvedi, V.; Manju, Y. K.; Sinha,
S. Bioorg. Med. Chem. Lett. 2008, 18, 289−292. (b) Gibson, H. W.;
Lee, S. H.; Engen, P. T.; Lecavalier, P.; Sze, J.; Shen, Y. X.; Bheda, M. J.
Org. Chem. 1993, 58, 3748−3756. (c) Finocchi, P.; Gust, D.; Mislow,
K. J. Am. Chem. Soc. 1974, 96, 3198−3205. (d) Nair, V.; Thomas, S.;
Mathew, S. C.; Abhilash, K. G. Tetrahedron 2006, 62, 6731−6747.
(4) (a) Nambo, M.; Crudden, C. M. Angew. Chem., Int. Ed. 2013, 53,
742−746. (b) Niwa, T.; Yorimitsu, H.; Oshima, K. Org. Lett. 2007, 9,
2373−2375. (c) Xia, Y.; Hu, F. D.; Liu, Z. X.; Qu, P. Y.; Ge, R.; Ma,
C.; Zhang, Y.; Wang, J. B. Org. Lett. 2013, 15, 1784−1787. (d) Cao, L.-
L.; Li, X.-N.; Meng, F.-Y.; Jiang, G.-F. Tetrahedron Lett. 2012, 53,
3873−3875. (e) McGrew, G. I.; Temaismithi, J.; Carroll, P. J.; Walsh,
P. J. Angew. Chem., Int. Ed. 2010, 49, 5541−5544. (f) Bellomo, A.;
Zhang, J.; Trongsiriwat, N.; Walsh, P. J. Chem. Sci. 2013, 4, 849−859.
(g) Zhang, J. D.; Bellomo, A.; Creamer, A. D.; Dreher, S. D.; Walsh, P.
J. J. Am. Chem. Soc. 2012, 134, 13765−13772.
(5) For the complementary approach employing racemic electro-
philes in a dynamic kinetic resolution approach, see: (a) Wilsily, A.;
Tramultola, F.; Owston, N. A.; Fu, G. C. J. Am. Chem. Soc. 2012, 134,
5794−5797. (b) Glasspoole, B. W.; Crudden, C. M. Nat. Chem. 2011,
3, 912−913.
(6) (a) Taylor, B. L. H.; Harris, M. R.; Jarvo, E. R. Angew. Chem., Int.
Ed. 2012, 51, 7790−7793. (b) Harris, M. R.; Hanna, L. E.; Greene, M.
A.; Moore, C. E.; Jarvo, E. R. J. Am. Chem. Soc. 2013, 135, 3303−3306.
(7) Zhou, Q.; Srinivas, H. D.; Dasgupta, S.; Watson, M. P. J. Am.
Chem. Soc. 2013, 135, 3307−3310.
(8) Shi, B. F.; Maugel, N.; Zhang, Y. H.; Yu, J. Q. Angew. Chem., Int.
Ed. 2008, 47, 4882−4886.
(9) Sun, F. L.; Zheng, X. J.; Gu, Q.; He, Q. L.; You, S. L. Eur. J. Org.
Chem. 2010, 47−50.
(10) Imao, D.; Glasspoole, B. W.; Laberge, V. S.; Crudden, C. M. J.
Am. Chem. Soc. 2009, 131, 5024−5025.
(11) (a) Glasspoole, B. W.; Ghozati, K.; Moir, J.; Crudden, C. M.
Chem. Commun. 2012, 48, 1230−1232. (b) Chausset-Boissarie, L.;
Ghozati, K.; LaBine, E.; Chen, J. L.-Y.; Aggarwal, V. K.; Crudden, C.
M. Chem.Eur. J. 2013, in press.
(12) Partridge, B. M.; Chausset-Boissarie, L.; Burns, M.; Pulis, A. P.;
Aggarwal, V. K. Angew. Chem., Int. Ed. 2012, 51, 11795−11799.
(13) Molander, G. A.; Wisniewski, S. R. J. Am. Chem. Soc. 2012, 134,
16856−16868.
D
dx.doi.org/10.1021/ja412159g | J. Am. Chem. Soc. XXXX, XXX, XXX−XXX