4686
Y. Yamamoto et al. / Tetrahedron 63 (2007) 4680–4687
(FAB): found m/z¼363.0920, calcd for C18H19O6S
M+1¼363.0902.
Acknowledgements
Financial support of a Grant-in-Aid for Scientific Research
(no. 16655012) from the Ministry of Education, Science,
Sports and Culture of Japan is gratefully acknowledged.
4.4.12. 1-Tosyloxy-2-octanone. Oil; IR (neat): 1180, 1360,
1590, 1730 cmꢂ1; 1H NMR (400 MHz, CDCl3): d¼0.87 (t,
J¼7.0 Hz, 3H), 1.20–1.32 (m, 6H), 1.48–1.62 (m, 2H),
2.45 (s, 3H), 2.49 (t, J¼7.2 Hz, 2H), 4.49 (s, 2H), 7.37 (d,
J¼8.0 Hz, 2H), 7.82 (d, J¼8.0 Hz, 2H); 13C NMR
(400 MHz, CDCl3): d¼13.97, 21.68, 22.39, 22.76, 28.62,
31.43, 38.98, 71.78, 128.04, 130.00, 132.30, 145.44,
203.43; HRMS (FAB): found m/z¼299.1295, calcd for
C15H23O4S M+1¼299.1317.
References and notes
1. Varvoglis, A. Hypervalent Iodine in Organic Synthesis;
Academic: San Diego, CA, 1997.
2. Reviews: (a) Ochiai, M. Rev. Heteroat. Chem. 1989, 2, 92; (b)
Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431; (c) Stang, P. J.
Angew. Chem., Int. Ed. Engl. 1992, 31, 274; (d) Prakash, O.;
Saini, N.; Sharma, P. K. Synlett 1994, 221; (e) Kitamura, T.
Yuki Gosei Kagaku Kyokaishi 1995, 53, 893; (f) Stang, P. J.;
Zhdankin, V. V. Chem. Rev. 1996, 96, 1123; (g) Umemoto, T.
Chem. Rev. 1996, 96, 1757; (h) Kita, Y.; Takada, T.; Tohma,
H. Pure Appl. Chem. 1996, 68, 627; (i) Togo, H.; Hoshina,
Y.; Nogami, G.; Yokoyama, M. Yuki Gosei Kagaku Kyokaishi
1997, 55, 90; (j) Varvoglis, A. Tetrahedron 1997, 53, 1179;
(k) Zhdankin, V. V. Rev. Heteroat. Chem. 1997, 17, 133; (l)
Muraki, T.; Togo, H.; Yokoyama, M. Rev. Heteroat. Chem.
1997, 17, 213; (m) Kitamura, T.; Fujiwara, Y. Org. Prep.
Proced. Int. 1997, 29, 409; (n) Varvoglis, A.; Spyroudis, S.
Synlett 1998, 221; (o) Zhdankin, V. V.; Stang, P. J.
Tetrahedron 1998, 54, 10927; (p) Moriarty, R. M.; Prakash,
O. Adv. Heterocycl. Chem. 1998, 69, 1; (q) Togo, H.;
Katohgi, M. Synlett 2001, 565; (r) Zhdankin, V. V.; Stang,
P. J. Chem. Rev. 2002, 102, 2523; (s) Richardson, R. D.;
Wirth, T. Angew. Chem., Int. Ed. 2006, 45, 4402.
4.4.13. 3-Tosyloxy-2-octanone. Oil; IR (neat): 1180, 1360,
1600, 1740 cmꢂ1; 1H NMR (400 MHz, CDCl3): d¼0.80 (t,
J¼7.3 Hz, 3H), 1.00–1.30 (m, 6H), 1.54–1.78 (m, 2H),
2.23 (s, 3H), 2.48 (s, 3H), 4.58 (dd, J¼8.4, 4.6 Hz, 1H),
7.36 (d, J¼8.7 Hz, 2H), 7.81 (d, J¼8.7 Hz, 2H); 13C NMR
(400 MHz, CDCl3): d¼13.91, 21.97, 22.35, 24.17, 26.01,
31.00, 31.52, 84.62, 128.13, 130.07, 132.98, 145.48,
205.78; HRMS (FAB): found m/z¼299.1315, calcd for
C15H23O4S M+1¼299.1317.
4.4.14. d-Tosyloxylevulinic acid ethyl ester. Oil; IR (neat):
1090, 1590, 1730 cmꢂ1 1H NMR (400 MHz, CDCl3):
;
d¼1.24 (t, J¼7.3 Hz, 3H), 2.46 (s, 3H), 2.61 (t, J¼6.3 Hz,
2H), 2.81 (t, J¼6.3 Hz, 2H), 4.12 (q, J¼7.3 Hz, 2H), 4.56
(s, 2H), 7.38 (d, J¼8.4 Hz, 2H), 7.83 (d, J¼8.4 Hz, 2H);
13C NMR (400 MHz, CDCl3): d¼14.13, 21.70, 27.42,
33.69, 60.85, 71.82, 128.08, 130.07, 132.20, 145.55,
172.16, 201.86; HRMS (FAB): found m/z¼315.0893, calcd
for C14H19O6S M+1¼315.0902.
3. Reviews: (a) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett
1990, 365; (b) Koser, G. F. Aldrichimica 2001, 34, 89; (c)
Prakash, O.; Saini, N.; Sharma, P. K. Heterocycles 1994, 38,
409; Papers: (d) Neilands, O.; Karele, B. J. Org. Chem. USSR
1970, 6, 885; (e) Koser, G. F.; Wettach, R. H.; Troup, J. M.;
Frenz, B. A. J. Org. Chem. 1976, 41, 3609; (f) Koser, G. F.;
Wettach, R. H. J. Org. Chem. 1977, 42, 1476; (g) Koser,
G. F.; Wettach, R. H.; Smith, C. S. J. Org. Chem. 1980, 45,
1543; (h) Koser, G. F.; Relenyi, A. G.; Kalos, A. N.;
Rebrovic, L.; Wettach, R. H. J. Org. Chem. 1982, 47, 2487;
(i) Moriarty, R. M.; Penmasta, R.; Awasthi, A. K.; Epa,
W. R.; Prakash, I. J. Org. Chem. 1989, 54, 1101; (j) Moriarty,
R. M.; Vaid, R. K.; Hopkins, T. E.; Vaid, B. K.; Prakash, O.
Tetrahedron Lett. 1990, 31, 201; (k) Tuncay, A.; Dustman,
J. A.; Fisher, G.; Tuncay, C. I. Tetrahedron Lett. 1992, 33,
7647; (l) Moriarty, R. M.; Vaid, B. K.; Duncan, M. P.; Levy,
S. G.; Prakash, O.; Goyal, S. Synthesis 1992, 845; (m)
Prakash, O.; Goyal, S. Synthesis 1992, 629; (n) Prakash, O.;
Rani, N.; Goyal, S. J. Chem. Soc., Perkin Trans. 1 1992, 707;
(o) See Ref. 2d; (p) Vrama, R. S.; Kumar, D.; Liesen, P. J.
J. Chem. Soc., Perkin Trans. 1 1998, 4093; (q) Lee, J. C.;
Choi, Ju.-H. Synlett 2001, 234.
4. Monomer reagents: (a) Muraki, T.; Togo, H.; Yokoyama, M.
J. Org. Chem. 1999, 64, 2883; (b) Nabana, T.; Togo, H.
J. Org. Chem. 2002, 67, 4362; (c) Misu, Y.; Togo, H. Org.
Biomol. Chem. 2003, 1, 1342; (d) Ueno, M.; Nabana, T.;
Togo, H. J. Org. Chem. 2003, 68, 6424; Polymer reagents:
(e) Abe, S.; Sakuratani, K.; Togo, H. Synlett 2001, 22; (f)
Abe, S.; Sakuratani, K.; Togo, H. J. Org. Chem. 2001, 66,
6174; (g) Sakuratani, K.; Togo, H. ARKIVOC 2003, 11; (h)
Ueno, M.; Togo, H. Synthesis 2004, 2673.
4.4.15. b-Tosyloxylevulinic acid ethyl ester. Oil; IR (neat):
1180, 1590, 1720 cmꢂ1 1H NMR (400 MHz, CDCl3):
;
d¼1.20 (t, J¼7.2 Hz, 3H), 2.29 (s, 3H), 2.48 (s, 3H), 2.75
(dd, J¼16.8, 5.4 Hz, 1H), 2.90 (dd, J¼16.8, 5.4 Hz, 1H),
4.06 (m, 2H), 4.98 (t, J¼5.4, 1H), 7.38 (d, J¼7.0 Hz, 2H),
7.83 (d, J¼7.0 Hz, 2H); 13C NMR (400 MHz, CDCl3):
d¼14.01, 21.75, 26.86, 36.85, 61.33, 79.65, 128.04,
130.11, 132.87, 145.67, 168.66, 204.47; HRMS (FAB):
found m/z¼315.0893, calcd for C14H19O6S M+1¼315.0902.
4.4.16. a-(p-Chlorobenzenesulfonyloxy)acetophenone.
Mp: 96 ꢀC (lit.13 97 ꢀC); IR (KBr): 1180, 1540,
1
1700 cmꢂ1; H NMR (400 MHz, CDCl3): d¼5.36 (s, 2H),
7.48 (t, J¼7.5 Hz, 2H), 7.56 (d, J¼8.9 Hz, 2H), 7.63 (t, J¼
8.9 Hz, 1H), 7.84 (d, J¼7.5 Hz, 2H), 7.92 (d, J¼8.9 Hz, 2H).
4.4.17. a-(Methanesulfonyloxy)acetophenone. Mp: 72–
74 ꢀC (lit.14 76–77 ꢀC); IR (KBr): 1185, 1520, 1710 cmꢂ1
;
1H NMR (400 MHz, CDCl3): d¼3.31 (s, 3H), 5.53 (s, 2H),
7.53 (t, J¼7.6 Hz, 2H), 7.66 (t, J¼7.6 Hz, 1H), 7.90 (d,
J¼7.6 Hz, 2H).
4.4.18. a-(Camphorsulfonyloxy)acetophenone. Oil (lit.15
1
60–61 ꢀC); IR (neat): 1170, 1590, 1720 cmꢂ1; H NMR
(400 MHz, CDCl3): d¼0.92 (s, 3H), 1.14 (s, 3H), 1.42–
1.51 (m, 1H), 1.74–1.85 (m, 1H), 1.95 (d, J¼18.6 Hz, 1H),
2.04–2.16 (m, 2H), 2.36–2.55 (m, 2H), 3.35 (d,
J¼15.3 Hz, 1H), 3.82 (d, J¼15.3 Hz, 1H), 5.53 (s, 2H),
7.52 (t, J¼7.2 Hz, 2H), 7.64 (t, J¼7.2 Hz, 1H), 7.92 (d,
J¼7.2 Hz, 2H).