R. Gnaneshwar et al. / Tetrahedron Letters 44 (2003) 6047–6049
6049
References
Soc., Perkin Trans. 1 1982, 1099–1104; (c) Bunce, R. A.;
Schlecht, M. F.; Dauben, W. G.; Heathcock, C. H.
Tetrahedron Lett. 1983, 24, 4943–4946; (d) Berl, V.;
Helmchen, G.; Preston, S. Tetrahedron Lett. 1994, 35,
233–236.
1
. (a) Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. Tetra-
hedron 1991, 47, 9773–9782; (b) Huffman, J. W.; Potnis,
S. M.; Satish, A. V. J. Org. Chem. 1985, 50, 4266–4270;
(
c) Otera, J.; Wakahara, Y.; Kamei, H.; Sato, T.; Nozaki,
15. Genisson, Y.; Gorrichon, L. Tetrahedron Lett. 2000, 41,
4881–4884.
16. Dicker, I. B.; Cohen, G. M.; Farnham, W. B.; Hertler,
W. R.; Laganis, E. D.; Sogah, D. Y. Macromolecules
H.; Fukuzumi, S. Tetrahedron Lett. 1991, 32, 2405–2408.
. Rajan Babu, T. V. J. Org. Chem. 1984, 49, 2083–2089
and references cited therein.
. Grieco, P. A.; Cooke, R. J.; Henry, K. J.; VanderRoest,
J. M. Tetrahedron Lett. 1991, 32, 4665–4668.
2
3
4
5
1990, 23, 4034–4041.
1
1
7. Brittain, W. J. J. Am. Chem. Soc. 1988, 110, 7440–7444.
8. Puranik, V. G.; Tavale, S. S.; Iyer, V. S.; Sehra, J. C.;
Sivaram, S. J. Chem. Soc., Perkin Trans. 2 1993, 1517–
. Bunce, R. A.; Schlecht, M. F.; Dauben, W. G.; Heath-
cock, C. H. Tetrahedron Lett. 1983, 4943–4946.
. (a) Kita, Y.; Segawa, J.; Haruta, J.; Fujii, T.; Tamura, Y.
Tetrahedron Lett. 1980, 21, 3779–3782; (b) Danishefsky,
S.; Vaughan, K.; Gadwood, R.; Tsuzuki, K. J. J. Am.
Chem. Soc. 1981, 103, 4136–4141; (c) Mukaiyama, T.;
Tamura, M.; Kobayashi, S. Chem. Lett. 1986, 1817–1818;
1
520.
1
9. Spectroscopic data of d-ketoester: 3a: light yellow liquid,
−1 1
FT-IR (neat); wmax 1732, 1699 cm ; H NMR (200 MHz,
CDCl ); l 1.11 (2s, separated by 3 Hz, 6H); 1.49–2.55 (m,
3
13
7H); 3.59 (s, 3H); C NMR (50 MHz, CDCl ); l 22.49
3
(d) Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H.; Kamei,
(
2C), 24.29, 38.63, 40.28, 43.70, 44.95, 51.56, 177.02,
H.; Fukuzumi, S. Tetrahedron Lett. 1991, 21, 2405–2408.
. (a) Matsumoto, K. Angew. Chem., Int. Ed. Eng. 1980, 19,
2
8
17.71; Anal. calcd for C H O (184.23); C, 65.19; H,
10 16 3
6
.75. Found: C, 65.07; H, 8.98. 3b: light yellow liquid,
1
013–1014; (b) Bunce, R. A.; Schlecht, M. F.; Dauben,
−1 1
FT-IR (neat); wmax 1734, 1716 cm ; H NMR (200 MHz,
CDCl ); l 1.19 (2s, separated by 3.9 Hz, 6H); 1.40–2.95
W. G.; Heathcock, C. H. Tetrahedron Lett. 1983, 24,
3
4
943–4946; (c) Matsumoto, K.; Uchida, T. Chem. Lett.
13
(
m, 9H); 3.60 (s, 3H);
C NMR (50 MHz, CDCl ); l
3
1
981, 1673–1676.
2
5
0.84, 21.09, 24.10, 25.35, 40.13, 42.26, 44.25, 44.91,
0.72, 176.21, 209.80. Anal. calcd for C H O (198.26);
7
8
. Saigo, K.; Osaki, M.; Mukaiyama, T. Chem. Lett. 1976,
63–164.
. (a) Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. J. Am.
Chem. Soc. 1991, 113, 4028–4030; (b) Fujita, Y.;
Fukuzumi, S.; Otera, J. Tetrahedron Lett. 1997, 38, 2117–
1
1
18
3
1
C, 66.64; H, 9.15. Found C, 66.76; H, 9.27. 3c: light
yellow liquid, FT-IR (neat) wmax 1734, 1712 cm ;
NMR (500 MHz, CDCl ); l 0.85 (s, 3H); 1.14 (s, 6H);
1
Hz, 1H); 2.17 (dd, J=7.1, 13.1 Hz, 1H); 2.28 (m, 1H);
2
MHz, CDCl ); l 19.11, 20.80 (2C), 21.50, 30.83, 36.86,
−1
1
H
3
.64 (m, 2H); 1.73 (m, 1H); 1.92 (m, 1H); 2.14 (d, J=13.5
2
120.
. Weghe, P.; Collin, J. Tetrahedron Lett. 1993, 34, 3881–
884.
9
1
3
.48 (d, J=13.5 Hz, 1H); 3.60 (s, 3H);
C NMR (125
3
3
1
0. (a) Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.;
Ishitani, H. Tetrahedron Lett. 1992, 33, 6815–6818; (b)
Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.;
Ishitani, H. Synlett 1993, 472–474; (c) Kobayashi, S.;
Horibe J. Am. Chem. Soc. 1994, 116, 9805–9806; (d)
Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59,
40.57, 42.45, 48.81, 51.34, 176.69, 211.90; Anal. calcd for
C H O (212.28); C, 67.89; H, 9.49. Found C, 67.98; H,
12
20
3
9.60. 3d: light yellow liquid, FT-IR (neat) w
1736, 1670
max
−
1 1
cm ; H NMR (500 MHz, CDCl ); l 0.90 (2s, separated
by 2.2 Hz, 6H); 0.94 (s, 3H); 1.15 (2s, separated by 5.2
Hz, 6H); 1.49 (d, J=14.3 Hz, 1H); 1.69 (d, J=14.3 Hz,
3
3
590–3596; (e) Kobayashi, S.; Hachiya, I.; Araki, M. J.
1
2
H); 2.11 (d, J=14.7 Hz, 2H); 2.15 (d, J=13.5 Hz, 1H);
.64 (d, J=13.9 Hz, 1H); 3.65 (s, 3H);
Org. Chem. 1994, 59, 3758–3759; (f) Kawada, A.; Mita-
mura, S.; Kobayashi, S. Chem. Commun. 1996, 183–184.
1. Grieco, P. A.; Dubay, W. J.; Todd, L. J. J. Org. Chem.
1
3
C NMR (125
MHz, CDCl ); l 20.68, 20.74, 22.95, 28.95, 34.31 (2C),
3
1
1
1
41.97, 44.11, 47.40, 49.86, 51.21, 52.91, 176.67, 212.02.
1
994, 59, 6898–6899.
Anal. calcd for C H O (240.34); C, 69.96; H, 10.06.
Found C, 70.0; H, 10.14. 5a: light yellow liquid, FT-IR
14
24
3
2. Fukuzumi, S.; Okamoto, T.; Yasui, K.; Suenobu, T.;
Itoh, S.; Otera, J. Chem. Lett. 1997, 667–668.
−
1
1
(
neat) wmax 1738, 1726 cm ; H NMR (200 MHz,
3. (a) Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem.
Soc. 1990, 112, 4595–4596; (b) Forman, M. A.; Dailey,
W. P. J. Am. Chem. Soc. 1991, 113, 2761–2762; (c)
Ipaktschi, J.; Heydari, A. Angew. Chem., Int. Ed. Engl.
CDCl ); l 1.07 (s, 6H); 1.69 (t, J=8.1 Hz, 2H); 2.04 (s,
3
1
3
3H); 2.31 (t, J=8.0 Hz, 2H); 3.56 (s, 3H); C NMR (50
MHz, CDCl ); l 24.84 (2C), 29.55, 33.70, 39.14, 41.31,
3
51.45, 177.50, 207.64. Anal. calcd for C H O (172.22);
1
992, 31, 313–314; (d) Grieco, P. A.; Collins, J. L.;
9 16 3
C, 62.76; H, 9.36. Found C, 62.36; H, 9.34. 5b: light
yellow liquid, FT-IR (neat) wmax 1734, 1723 cm ;
NMR (200 MHz, CDCl ); l 0.98 (s, 6H); 1.08 (s, 6H);
2
Henry, Jr. Tetrahedron Lett. 1992, 33, 4735–4738; (e)
Grieco, P. A.; Cooke, R. J.; Henry, K. J.; VanderRoest,
J. M. Tetrahedron Lett. 1991, 32, 4665–4668; (f) Reetz,
M. T.; Raguse, B.; Marth, C. F.; Hugel, H. M.; Bach, T.;
Fox, D. N. A. Tetrahedron Lett. 1993, 34, 1119–1122.
4. (a) Kita, Y.; Segawa, J.; Haruta, J.; Fujii, T.; Tamura, Y.
Tetrahedron Lett. 1980, 21, 3779–3782; (b) Kita, Y.;
Segawa, J.; Haruta, J.; Yasuda, H.; Tamura, Y. J. Chem.
−
1
1
H
3
1
3
.08 (s, 3H); 2.42 (s, 2H); 3.59 (s, 3H);
C NMR (50
MHz, CDCl ); l 21.02 (2C), 22.05 (2C), 32.85, 38.04,
3
48.88, 49.32, 51.34, 177.13, 208.92. Anal. calcd for
1
C H O
H, 9.97.
(200.27); C, 65.96; H, 10.06. Found C, 65.69;
11 20 3