-
1
-
-
0001084079
-
-
Reviews: (a) Duhamel, L.; Duhamel, P.; Launay, J.-C.; Plaquevent, J.-C. Bull. Soc. Chim. Fr. 1984, 11, 421-430.
-
(1984)
Bull. Soc. Chim. Fr.
, vol.11
, pp. 421-430
-
-
Duhamel, L.1
Duhamel, P.2
Launay, J.-C.3
Plaquevent, J.-C.4
-
4
-
-
0034679019
-
-
For recent examples of stoichimetric enantioselective protonation of lithium enolates, see: (a) Vedejs, E.; Kruger, A. W. Lee, N.; Sakata, S. T.; Stec, M.; Suna, E. J. Am. Chem. Soc. 2000, 122, 4602-4607.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 4602-4607
-
-
Vedejs, E.1
Kruger, A.W.2
Lee, N.3
Sakata, S.T.4
Stec, M.5
Suna, E.6
-
5
-
-
0041444854
-
-
(b) Yasuhito, Y.; Yoshihiro, E.; Kazunori, O.; Kenji, K. Tetrahedron Lett. 2000, 41, 209-213.
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 209-213
-
-
Yasuhito, Y.1
Yoshihiro, E.2
Kazunori, O.3
Kenji, K.4
-
6
-
-
0032741251
-
-
(c) Vedejs, E.; Kruger, A. W.; Suna, E. J. Org. Chem. 1999, 64, 7863-7870.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 7863-7870
-
-
Vedejs, E.1
Kruger, A.W.2
Suna, E.3
-
7
-
-
0033553373
-
-
(d) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939-3940.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 3939-3940
-
-
Asensio, G.1
Cuenca, A.2
Gavina, P.3
Medio-Simon, M.4
-
8
-
-
0032703585
-
-
(e) Yanagisawa, A.; Kikuchi, T.; Watanabe, T.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1999, 72, 2337-2343.
-
(1999)
Bull. Chem. Soc. Jpn.
, vol.72
, pp. 2337-2343
-
-
Yanagisawa, A.1
Kikuchi, T.2
Watanabe, T.3
Yamamoto, H.4
-
10
-
-
0032540964
-
-
(g) Prat, L.; Mojovic, L.; Levacher, V.; Dupas, G.; Queguiner, G.; Bourguignon, J. Tetrahedron: Asymmetry 1998, 9, 2509-2516.
-
(1998)
Tetrahedron: Asymmetry
, vol.9
, pp. 2509-2516
-
-
Prat, L.1
Mojovic, L.2
Levacher, V.3
Dupas, G.4
Queguiner, G.5
Bourguignon, J.6
-
11
-
-
0030679752
-
-
(h) Martin, J.; Lansne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181-7182.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 7181-7182
-
-
Martin, J.1
Lansne, M.-C.2
Plaquevent, J.-C.3
Duhamel, L.4
-
12
-
-
0030773296
-
-
(i) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293-3308.
-
(1997)
Tetrahedron: Asymmetry
, vol.8
, pp. 3293-3308
-
-
Takahashi, T.1
Nakao, N.2
Koizumi, T.3
-
13
-
-
0030839482
-
-
(j) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron 1997, 38, 6861-6864.
-
(1997)
Tetrahedron
, vol.38
, pp. 6861-6864
-
-
Kosugi, H.1
Hoshino, K.2
Uda, H.3
-
15
-
-
0000795285
-
-
(l) Fuji, K.; Kawabata, T.; Kuroda, A. J. Org. Chem. 1995, 60, 1914-1915.
-
(1995)
Org. Chem.
, vol.60
, pp. 1914-1915
-
-
Fuji, K.1
Kawabata, T.2
Kuroda, A.J.3
-
16
-
-
33748244251
-
-
(m) Yanagisawa, A.; Kuribayashi, T.; Kikichi, T.; Yamamoto, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 107-109.
-
(1994)
Angew. Chem., Int. Ed. Engl.
, vol.33
, pp. 107-109
-
-
Yanagisawa, A.1
Kuribayashi, T.2
Kikichi, T.3
Yamamoto, H.4
-
17
-
-
0001178183
-
-
(n) Vedejs, E.; Lee, N.; Sakata, S. T. J. Am. Chem. Soc. 1994, 116, 2175-2176.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 2175-2176
-
-
Vedejs, E.1
Lee, N.2
Sakata, S.T.3
-
18
-
-
0028339133
-
-
(o) Cavelier, F.; Gomez, S.; Jacquier, R.; Verducci, J. Tetrahedron Lett. 1994, 35, 2891-2894.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 2891-2894
-
-
Cavelier, F.1
Gomez, S.2
Jacquier, R.3
Verducci, J.4
-
19
-
-
0001686004
-
-
(p) Gerlach, U.; Haubenreich, T.; Hünig, S. Chem. Ber. 1994, 127, 1981-1988.
-
(1994)
Chem. Ber.
, vol.127
, pp. 1981-1988
-
-
Gerlach, U.1
Haubenreich, T.2
Hünig, S.3
-
20
-
-
0013519358
-
-
(q) Gerlach, U.; Haubenreich, T.; Hünig, S. Chem. Ber. 1994, 127, 1989-1992.
-
(1994)
Chem. Ber.
, vol.127
, pp. 1989-1992
-
-
Gerlach, U.1
Haubenreich, T.2
Hünig, S.3
-
21
-
-
0027456369
-
-
(r) Fuji, K.; Tanaka, K.; Miyamoto, H. Tetrahedron: Asymmetry 1993, 4, 247-259.
-
(1993)
Tetrahedron: Asymmetry
, vol.4
, pp. 247-259
-
-
Fuji, K.1
Tanaka, K.2
Miyamoto, H.3
-
23
-
-
33748234317
-
-
(t) Fehr, C.; Stempt, I.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1042-1044.
-
(1993)
Angew. Chem., Int. Ed. Engl.
, vol.32
, pp. 1042-1044
-
-
Fehr, C.1
Stempt, I.2
Galindo, J.3
-
25
-
-
0034685934
-
-
For recent examples of catalytic enantioselective protonation of lithium enolates, see: (a) Yanagisawa, A.; Watanebe, T.; Kikuchi, T.; Yamamoto, H. J. Org. Chem. 2000, 65, 2979-2983.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 2979-2983
-
-
Yanagisawa, A.1
Watanebe, T.2
Kikuchi, T.3
Yamamoto, H.4
-
26
-
-
0032486155
-
-
(b) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847-1850.
-
(1998)
Tetrahedron: Asymmetry
, vol.9
, pp. 1847-1850
-
-
Aboulhoda, S.J.1
Reiners, I.2
Wilken, J.3
Hénin, F.4
Martens, J.5
Muzart, J.6
-
28
-
-
0029120266
-
-
(d) Aboulhoda, S. J.; Letinois, S.; Wilken, J.; Reiners, I.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1995, 6, 1865-1868.
-
(1995)
Tetrahedron: Asymmetry
, vol.6
, pp. 1865-1868
-
-
Aboulhoda, S.J.1
Letinois, S.2
Wilken, J.3
Reiners, I.4
Hénin, F.5
Martens, J.6
Muzart, J.7
-
29
-
-
84988467033
-
-
(e) Yanagisawa, A.; Kikichi, K.; Watanabe, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1995, 372-374.
-
(1995)
Synlett
, pp. 372-374
-
-
Yanagisawa, A.1
Kikichi, K.2
Watanabe, T.3
Kuribayashi, T.4
Yamamoto, H.5
-
31
-
-
0028074395
-
-
(g) Aboulhoda, S. J.; Hénin, F.; Muzart, J. Thorey, C.; Behnem, W.; Martens, J.; Mehler, T. Tetrahedron: Asymmetry 1994, 5, 1321-1326.
-
(1994)
Tetrahedron: Asymmetry
, vol.5
, pp. 1321-1326
-
-
Aboulhoda, S.J.1
Hénin, F.2
Muzart, J.3
Thorey, C.4
Behnem, W.5
Martens, J.6
Mehler, T.7
-
32
-
-
33748233583
-
-
(h) Fehr, C.; Stempf, I.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1044-1046.
-
(1993)
Angew. Chem., Int. Ed. Engl.
, vol.32
, pp. 1044-1046
-
-
Fehr, C.1
Stempf, I.2
Galindo, J.3
-
33
-
-
0034645732
-
-
For examples of asymmetric protonation of samarium enolates, see: (a) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Curran, D. P. Tetrahedron 2000, 56, 351-356.
-
(2000)
Tetrahedron
, vol.56
, pp. 351-356
-
-
Nakamura, Y.1
Takeuchi, S.2
Ohgo, Y.3
Curran, D.P.4
-
34
-
-
0033538074
-
-
(b) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595-4620.
-
(1999)
Tetrahedron
, vol.55
, pp. 4595-4620
-
-
Nakamura, Y.1
Takeuchi, S.2
Ohgo, Y.3
Yamaoka, M.4
Yoshida, A.5
Mikami, K.6
-
35
-
-
0001935717
-
-
(c) Mikami, K.; Yamaoka, M.; Yoshida, A.; Nakamura, Y.; Takeuchi, S.; Ohgo, Y. Synlett 1998, 607-608.
-
(1998)
Synlett
, pp. 607-608
-
-
Mikami, K.1
Yamaoka, M.2
Yoshida, A.3
Nakamura, Y.4
Takeuchi, S.5
Ohgo, Y.6
-
36
-
-
0032547976
-
-
(d) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691-8694.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 8691-8694
-
-
Takeuchi, S.1
Nakamura, Y.2
Ohgo, Y.3
Curran, D.P.4
-
37
-
-
0030901984
-
-
(e) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yomaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron Lett. 1997, 38, 2709-2712.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 2709-2712
-
-
Nakamura, Y.1
Takeuchi, S.2
Ohgo, Y.3
Yomaoka, M.4
Yoshida, A.5
Mikami, K.6
-
38
-
-
0029921615
-
-
(f) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805-2808.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 2805-2808
-
-
Nakamura, Y.1
Takeuchi, S.2
Ohira, A.3
Ohgo, Y.4
-
39
-
-
0028060419
-
-
(g) Takeuchi, S.; Ohira, A.; Miyoshi, N.; Mashio, H.; Ohgo, Y.; Tetrahedron: Asymmetry 1994, 5, 1763-1780.
-
(1994)
Tetrahedron: Asymmetry
, vol.5
, pp. 1763-1780
-
-
Takeuchi, S.1
Ohira, A.2
Miyoshi, N.3
Mashio, H.4
Ohgo, Y.5
-
41
-
-
0034720960
-
-
Xu, M.-H.; Wang, W.; Lin, G.-Q. Org. Lett. 2000, 2, 2229-2232.
-
(2000)
Org. Lett.
, vol.2
, pp. 2229-2232
-
-
Xu, M.-H.1
Wang, W.2
Lin, G.-Q.3
-
42
-
-
37049077893
-
-
(a) Fukuzawa, S.; Nakanishi, A.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commun. 1986, 624-625.
-
(1986)
J. Chem. Soc., Chem. Commun.
, pp. 624-625
-
-
Fukuzawa, S.1
Nakanishi, A.2
Fujinami, T.3
Sakai, S.4
-
43
-
-
37049066360
-
-
(b) Fukuzawa, S.; Nakanishi, A.; Fujinami, T.; Sakai, S. J. Chem. Soc., Perkin Trans. 1 1988, 1669-1675.
-
(1988)
J. Chem. Soc., Perkin Trans. 1
, vol.1
, pp. 1669-1675
-
-
Fukuzawa, S.1
Nakanishi, A.2
Fujinami, T.3
Sakai, S.4
-
44
-
-
85037519560
-
-
note
-
It has been reported that extremely high enantioselectivity (99%) was obtained in the enantioselective protonation of a lithium enolate of a thiol ester by using N-isopropylephedrine as a chiral proton source, see: refs 2t and 3h.
-
-
-
-
45
-
-
1442294351
-
-
Otsubo, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 5763-5764.
-
(1986)
Tetrahedron Lett.
, vol.27
, pp. 5763-5764
-
-
Otsubo, K.1
Inanaga, J.2
Yamaguchi, M.3
-
46
-
-
85037512601
-
-
note
-
The enantioselectivity was lowered when 4.0 equiv of HMPA was used in the reaction. For example, with this amount of HMPA as an additive, only 13% ee was obtained in the case of protonation using 8 as the chiral proton source.
-
-
-
-
47
-
-
85037492231
-
-
note
-
Due to the high oxophilicity and high coordination number of samarium, the chiral proton source, HMPA, and solvent THF are probably coordinated to the samarium ion in the transition state.
-
-
-
-
48
-
-
85037511771
-
-
note
-
2: C 80.93, H 6.39. Found: C 80.73, H 6.50.
-
-
-
-
49
-
-
0000478917
-
-
One important strategy for preparing α-substituted-γ-butyrolactone is stereoselective alkylation of lithium enolate of γ-butyrolactone, for examples, see: (a) Hanessian, S.; Murray, P. J. Org. Chem. 1987, 52, 1170-1172.
-
(1987)
J. Org. Chem.
, vol.52
, pp. 1170-1172
-
-
Hanessian, S.1
Murray, P.2
-
50
-
-
0024322415
-
-
(b) Chamberlin, A. R.; Dezube, M.; Reich, S. H.; Sall, D. J. J. Am. Chem. Soc. 1989, 111, 6247-6256.
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 6247-6256
-
-
Chamberlin, A.R.1
Dezube, M.2
Reich, S.H.3
Sall, D.J.4
-
51
-
-
0027296579
-
-
(c) Yamazaki, T.; Mizutani, K.; Kiyazume, T. J. Org. Chem. 1993, 58, 4346-4359.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 4346-4359
-
-
Yamazaki, T.1
Mizutani, K.2
Kiyazume, T.3
-
52
-
-
0001275802
-
-
(d) Clive, D. L. J.; Manning, H. W.; Boivin, T. L. B.; Postema, M. H. D. J. Org. Chem. 1993, 58, 6857-6873.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 6857-6873
-
-
Clive, D.L.J.1
Manning, H.W.2
Boivin, T.L.B.3
Postema, M.H.D.4
-
53
-
-
0029801091
-
-
(e) Moritani, Y.; Fukushima, C.; Ukita, T.; Miyagishima, T.; Ohmizu, H.; Iwasaki, T. J. Org. Chem. 1996, 61, 6922-6930.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 6922-6930
-
-
Moritani, Y.1
Fukushima, C.2
Ukita, T.3
Miyagishima, T.4
Ohmizu, H.5
Iwasaki, T.6
-
54
-
-
0001337069
-
-
(f) Pellissier, H.; Michellys, P. Y.; Santelli, M. J. Org. Chem. 1997, 62, 5588-5591.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 5588-5591
-
-
Pellissier, H.1
Michellys, P.Y.2
Santelli, M.3
|