M. D. Mihovilovic, M. E. Mrstik, C. A. Martinez and J. D. Stewart,
New J. Chem., 1999, 23, 827; (b) S. D. Doig, L. M. O’Sullivan, S. Patel,
J. M. Ward and J. M. Woodley, Enzyme Microb. Technol., 2001, 28,
265.
7 For a Saccharomyces cerevisiae expression system see: J. D. Stewart,
K. W. Reed and M. M. Kayser, J. Chem. Soc., Perkin Trans. 1, 1996,
755.
8 M. D. Mihovilovic, F. Rudroff, B. Gr o¨ tzl, P. Kapitan, R. Snajdrova,
J. Rydz and R. Mach, Angew. Chem., Int. Ed., 2005, 44, 3609.
9 (a) H. Iwaki, Y. Hasegawa, P. C. K. Lau, S. Wang and M. M. Kayser,
Appl. Environ. Microbiol., 2002, 68, 5681; (b) M. Griffin and
P. W. Trudgill, Eur. J. Biochem., 1976, 63, 199.
0 M. D. Mihovilovic, R. Snajdrova, A. Winninger and F. Rudroff,
Synlett, 2005, 2751.
1 (a) M. D. Mihovilovic, B. Gr o¨ tzl, W. Kandiller, R. Snajdrova,
A. Muskotal, D. A. Bianchi and P. Stanetty, Adv. Synth. Catal., 2006,
348, 463; (b) A. M. Montana and P. M. Grima, Tetrahedron Lett., 2001,
Notes and references
§
Physical and spectral properties of selected compounds. 6: colorless crystals,
1
mp: 78–80 uC; H-NMR (200 MHz, CDCl
1
3
) d 2.92 (dd, 2H, J 5 3.8 and
6.5 Hz), 3.05 (dd, 1H, J 5 2.5 and 16.5 Hz), 3.76 (s, 2H), 4.19 (dd, 1H,
13
J 5 2.7 and 3.6 Hz), 4.20–4.50 (m, 2H); C-NMR (50 MHz, CDCl
3
)
d 41.9 (t), 52.6 (d), 54.2 (d), 69.3 (d), 71.3 (t), 74.2 (d), 171.5 (s). 7: colorless
oil; H-NMR (200 MHz, CDCl ) d 2.43 (br s, 1H), 2.57 (d, 2H, J 5 7.5 Hz),
1
3
3.67 (s, 3H), 3.50–3.75 (m, 4H), 4.11 (t, 1H, J 5 4.3 Hz), 4.43 (t, 1H,
J 5 7.5 Hz); C-NMR (50 MHz, CDCl
13
3
) d 38.2 (t), 52.1 (d), 58.6 (d), 59.9
(
d), 62.7 (t), 74.8 (q), 79.7 (d), 171.2 (s). 9: beige oil, which slowly solidified,
1
mp 84–86 uC; H-NMR (400 MHz, CDCl
J 5 3.3 Hz), 3.62 (dd, 1H, J 5 4.6 and 12.4 Hz), 3.80 (dd, 1H, J 5 3.0 and
2.4 Hz), 4.15 (dd, 1H, J 5 2.1 and 7.5 Hz), 4.27 (ddd, 1H, J 5 3.0, 4.6 and
3
) d 1.79 (br s, 1H), 2.72 (d, 2H,
1
1
13
7
(
1
.5 Hz), 4.75–4.82 (m, 1H), 5.15 (dd, 1H, J 5 2.1 and 4.5 Hz); C-NMR
100 MHz, CDCl ) d 20.0 (d), 36.2 (t), 61.2 (t), 78.2 (d), 90.7 (d), 92.8 (d),
73.8 (s).
1
3
42, 7809.
1
2
For general reviews on Baeyer–Villiger reactions see: (a) G. R. Krow,
Org. React., 1993, 43, 251; (b) M. Renz and B. Meunier, Eur. J. Org.
Chem., 1999, 737.
For reviews on stereoselective Baeyer–Villiger oxidations see: (a)
M. D. Mihovilovic, F. Rudroff and B. Gr o¨ tzl, Curr. Org. Chem.,
12 For an excellent review on biocatalytic desymmetrizations see: E. Garcia-
Urdiales, I. Alfonso and V. Gotor, Chem. Rev., 2005, 105, 313.
13 (a) F. Rudroff, V. Alphand, R. Furstoss and M. D. Mihovilovic, Org.
Process Res. Dev., 2006, 10, 599; (b) M.-C. Guti e` rrez, R. Furstoss and
V. Alphand, Adv. Synth. Catal., 2005, 347, 1051; (c) I. Hilker,
M. C. Gutierrez, V. Alphand, R. Wohlgemuth and R. Furstoss, Org.
Lett., 2004, 6, 1955.
2
004, 8, 1057; (b) C. Bolm, in Peroxide Chemistry, ed. W. Adam, Wiley-
VCH: Weinheim, 2000, p. 494; (c) G. Strukul, Angew. Chem., Int. Ed.,
998, 37, 1198.
1
1
4 (a) T. Sato, Y. Hayakawa and R. Noyori, Bull. Chem. Soc. Jpn., 1984,
7, 2515; (b) R. Noyori, T. Sato and Y. Hayakawa, J. Am. Chem. Soc.,
978, 100, 2561; (c) T. Sato, R. Ito, Y. Hayakawa and R. Noyori,
Tetrahedron Lett., 1978, 21, 1829.
5 K. A. Cruickshank and C. B. Reese, Synthesis, 1983, 3, 199.
6 (a) K. R. Darnall, L. B. Townsend and R. K. Robins, Proc. Natl. Acad.
3
4
For recent reviews see: (a) N. M. Kamerbeek, D. B. Janssen, W. J. H. van
Berkel and M. W. Fraaije, Adv. Synth. Catal., 2003, 345, 667; (b)
M. D. Mihovilovic, B. M u¨ ller and P. Stanetty, Eur. J. Org. Chem., 2002,
5
1
3711.
1
1
(a) D. Bonsor, S. F. Butz, J. Solomons, S. Grant, I. J. S. Fairlamb,
M. J. Fogg and G. Grogan, Org. Biomol. Chem., 2006, 4, 1252; (b)
M. W. Fraaije, N. M. Kamerbeek, A. J. Heidekamp, R. Fortin and
D. B. Janssen, J. Biol. Chem., 2004, 279, 3354; (c) J. B. van Beilen,
F. Mourlane, M. A. Seeger, J. Kovac, Z. Li, T. H. M. Smits, U. Fritsche
and B. Witholt, Environ. Microbiol., 2003, 5, 174; (d) P. Brzostowicz,
D. M. Walters, S. M. Thomas, V. Nagarajan and P. E. Rouviere, Appl.
Environ. Microbiol., 2003, 69, 334; (e) M. W. Fraaije, N. M. Kamerbeek,
W. J. H. van Berkel and D. B. Janssen, FEBS Lett., 2002, 518, 43; (f)
P. C. Brzostowicz, K. L. Gibson, S. M. Thomas, M. S. Blasko and
P. E. Rouviere, J. Bacteriol., 2000, 182, 4241.
(a) M. D. Mihovilovic, F. Rudroff, A. Winninger, T. Schneider,
F. Schulz and M. T. Reetz, Org. Lett., 2006, 8, 1221; (b) M. Bocola,
F. Schulz, F. Leca, A. Vogel, M. W. Fraaije and M. T. Reetz, Adv.
Synth. Catal., 2005, 347, 979; (c) M. T. Reetz, B. Brunner, T. Schneider,
F. Schulz, C. M. Clouthier and M. M. Kayser, Angew. Chem., Int. Ed.,
Sci. U. S. A., 1967, 57, 548; (b) H. Nishimura, M. Mayama,
Y. Komatsu, H. Sato, N. Shimaoka and Y. Tanaka, J. Antibiot., Ser.
A., 1964, 17, 148.
17 E. A. Anderson, A. B. Holmes and I. Collins, Tetrahedron Lett., 2000,
41, 117.
1
8 S. Lochynski, B. Frackowiak, T. Olejniczak, Z. Ciunik and
C. Warwrzenczyk, Tetrahedron: Asymmetry, 2002, 13, 1761.
1
9 C. Cagnolini, M. Ferri, P. R. Jones and P. J. Murphy, Tetrahedron,
997, 53, 4815.
0 (a) P. J. Murphy and S. T. Dennison, Tetrahedron, 1993, 49, 6695; (b)
P. J. Murphy, J. Chem. Soc., Chem. Commun., 1992, 1096.
1
2
5
6
2
1 (a) D. J. Faulkner, Nat. Prod. Rep., 1984, 1, 251; (b) T. Suzuki,
K. Koizumi, H. Suzuki and E. Kurosawa, Chem. Lett., 1983, 1643.
22 R. R. Gadikota, C. S. Callam and T. L. Lowary, J. Org. Chem., 2001,
66, 9046.
2004, 43, 4078.
For the first E. coli based expression systems for BVMOs utilized in
whole-cell biocatalysis see: (a) G. Chen, M. M. Kayser,
23 H. B. Mereyala and R. R. Gadikota, Tetrahedron: Asymmetry, 2000, 11,
743.
3
216 | Chem. Commun., 2006, 3214–3216
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