Table 2 Evaluation of the substrate scope
in Comprehensive Asymmetric Catalysis, ed. E. N. Jacobsen, A. Pfaltz
and H. Yamamoto, Springer, New York, 1999, p. 649;
(d) E. N. Jacobsen, Acc. Chem. Res., 2000, 33, 421.
7 (a) M. Tokunaga, J. F. Larrow, F. Kakiuchi and E. N. Jacobsen,
Science, 1997, 277, 936; (b) S. E. Schaus, B. D. Brandes, J. F. Larrow,
M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow and
E. N. Jacobsen, J. Am. Chem. Soc., 2002, 124, 1307.
8 For related methodologies see: W. Hirahata, R. M. Thomas,
E. B. Lobkovsky and G. W. Coates, J. Am. Chem. Soc., 2008,
130, 17658.
9 (a) J. P. Collman, Z. Wang, A. Straumanis, M. Quelquejeu and
E. Rose, J. Am. Chem. Soc., 1999, 121, 460; (b) E. Rose,
B. Andrioletti, S. Zrig and M. Quelquejeu-Etheve, Chem. Soc.
Rev., 2005, 34, 573.
Entry
1c
Substrate
Product
Yielda (%)
eeb (%)
95
95
2c
3d
4d
5d
92
89
80
88
95
93
72
10 (a) K. Matsumoto, Y. Sawada, B. Saito, K. Sakai and T. Katsuki,
Angew. Chem., Int. Ed., 2005, 44, 4935; (b) Y. Sawada, K. Matsumoto
and T. Katsuki, Angew. Chem., Int. Ed., 2007, 46, 4559.
11 M. Colladon, A. Scarso, P. Sgarbossa, R. A. Michelin and
G. Strukui, J. Am. Chem. Soc., 2006, 128, 14006.
12 (a) M. Hickey, D. Goeddel, Z. Crane and Y. Shi, Proc. Natl. Acad.
Sci. U. S. A., 2004, 101, 5794; For biocatalytic methods see:
(b) K. Furuhashi, Biological Routes to Optically Active Epoxides,
Wiley, New York, 1992, p. 167.
13 Representative examples: (a) M. Amatore, T. D. Beeson,
S. P. Brown and D. W. MacMillan, Angew. Chem., Int. Ed.,
2009, 48, 5121; (b) M. Marigo, T. B. Poulsen, W. Zhang and
K. A. Jørgensen, J. Am. Chem. Soc., 2004, 126, 4790.
14 Reviews: (a) V. K. Aggarwal and C. L. Winn, Acc. Chem. Res.,
2004, 37, 611; (b) E. M. McGarrigle, E. L. Myers, O. Illa,
M. A. Shaw, S. L. Riches and V. K. Aggarwal, Chem. Rev.,
2007, 107, 5841.
82
81
90
15 Representative examples: (a) N. Furukawa, Y. Sugihara and
H. Fujihara, J. Org. Chem., 1989, 54, 4222; (b) V. K. Aggarwal,
H. Abdel-Rahman, R. V. H. Jones, H. Y. Lee and B. D. Reid,
J. Am. Chem. Soc., 1994, 116, 5973; (c) V. K. Aggarwal, J. G. Ford,
A. Thompson, R. V. H. Jones and M. C. H. Standen, J. Am. Chem.
Soc., 1996, 118, 7004; (d) J. Zanardi, C. Leriverend, D. Aubert,
K. Julienne and P. Metzner, J. Org. Chem., 2001, 66, 5620;
(e) C. L. Winn, B. R. Bellenie and J. M. Goodman, Tetrahedron
Lett., 2002, 43, 5427; (f) V. K. Aggarwal, E. Alonso, I. Bae,
G. Hynd, K. M. Lydon, M. J. Palmer, M. Patel, M. Porcelloni,
J. Richardson, R. A. Stenson, J. R. Studley, J. L. Vasse and
C. L. Winn, J. Am. Chem. Soc., 2003, 125, 10926; (g) M. Davoust,
J. F. Briere, P. A. Jaffres and P. Metzner, J. Org. Chem., 2005,
70, 4166; (h) X. –M. Deng, P. Cai, S. Ye, X. –L. Sun, W. –W. Liao,
K. Li, Y. Tang, Y. –D. Wu and L.-X. Dai, J. Am. Chem. Soc., 2006,
128, 9730; (i) J. Bi and V. K. Aggarwal, Chem. Commun., 2008, 120.
16 Shibasaki et al. found that chiral La-complexes can catalyse the
enantioselective epoxidation of ketones with superstoichiometric
sulfoxonium methylide: T. Sone, A. Yamaguchi, S. Matsunaga and
M. Shibasaki, J. Am. Chem. Soc., 2008, 130, 10078.
17 B. M. Trost and R. F. Hammen, J. Am. Chem. Soc., 1973, 95, 962.
18 L. Breau and T. Durst, Tetrahedron: Asymmetry, 1991, 2, 367.
19 B. R. Bellenie and J. M. Goodman, Chem. Commun., 2004, 1076.
20 (a) V. K. Aggarwal, A. Ali and M. P. Coogan, J. Org. Chem., 1997,
62, 8628; (b) V. K. Aggarwal, M. P. Coogan, R. A. Stenson, R. V. H.
Jones, R. Fieldhouse and J. Blacker, Eur. J. Org. Chem., 2002, 319.
21 Early claims involving the use of chiral phase-transfer catalysts
(ref. 21a,b) were later shown (ref. 21c) to be in error:
(a) T. Hiyama, T. Mishima, H. Sawada and H. Nozaki, J. Am.
Chem. Soc., 1975, 97, 1626; (b) Y. Zhang and W. Wu, Tetrahedron:
Asymmetry, 1997, 8, 2723; (c) S. A. Kavanagh and S. J. Connon,
Tetrahedron: Asymmetry, 2008, 19, 1414.
6c
7d
8d
75
94
91
92
90
9d,e
92
a
b
Isolated yields. Determined by CSP-HPLC. Using (R,R)–7f.
e
Using (S,S)–7f. 0.015 M reaction concentration.
c
d
problematic in reactions which rely on olefin oxidation
chemistry.
Financial support from Science Foundation Ireland is grate-
fully acknowledged. We thank Dr J. Goodman for helpful
discussions.
Notes and references
1 R. M. Hanson and K. B. Sharpless, J. Org. Chem., 1986, 51, 1922.
2 R. A. Johnson and K. B. Sharpless, in Catalytic Asymmetric Synthesis,
ed. I. Ojima, VCH, New York, 1993, p. 101.
3 W. Zhang, J. L. Loebach, S. R. Wilson and E. N. Jacobsen, J. Am.
Chem. Soc., 1990, 112, 2801.
4 R. Irie, K. Noda, Y. Ito, N. Matsumoto and T. Katsuki, Tetrahedron
Lett., 1990, 31, 7345.
5 E. M. McGarrigle and D. G. Gilheany, Chem. Rev., 2005,
105, 1563.
6 (a) M. Palucki, P. J. Pospisil, W. Zhang and E. N. Jacobsen, J. Am.
Chem. Soc., 1994, 116, 9333; (b) E. N. Jacobsen and M. H. Wu, in
Comprehensive Asymmetric Catalysis, ed. E. N. Jacobsen, A. Pfaltz
and H. Yamamoto, Springer, New York, 1999, p. 621; (c) T. Katsuki,
22 Aminosulfoxonium and sulfimide ylide precursors: (a) S. S. Taj,
A. C. Shah, D. Lee, G. Newton and R. Soman, Tetrahedron:
Asymmetry, 1995, 6, 1731; (b) C. P. Baird and P. C. Taylor,
J. Chem. Soc., Perkin Trans. 1, 1998, 3399.
23 A. Piccinini, S. A. Kavanagh, P. B. Connon and S. J. Connon, Org.
Lett., 2010, 12, 608.
24 Related work: (a) S. A. Kavanagh, A. Piccinini, E. M. Fleming and
S. J. Connon, Org. Biomol. Chem., 2008, 6, 1339; (b) S. A. Kavanagh,
A. Piccinini and S. J. Connon, Adv. Synth. Catal., 2010, 352, 2089.
c
7816 Chem. Commun., 2012, 48, 7814–7816
This journal is The Royal Society of Chemistry 2012