-
3
-
-
0000836416
-
-
Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
-
(a) Kemp, J. E. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol.3, pp 471-513.
-
(1991)
Comprehensive Organic Synthesis
, vol.3
, pp. 471-513
-
-
Kemp, J.E.G.1
-
7
-
-
0034720957
-
-
(a) Li, G.; Wei, H. X.; Kim, S. H. Org. Lett. 2000, 2, 2249-2252.
-
(2000)
Org. Lett.
, vol.2
, pp. 2249-2252
-
-
Li, G.1
Wei, H.X.2
Kim, S.H.3
-
8
-
-
0242330818
-
-
(b) Karur, S.; Kott, S. R. S. S.; Xu, X.; Canno, J. F.; Headley, A. D.; Li, G. J. Am. Chem. Soc. 2003, 125, 13340-13341.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 13340-13341
-
-
Karur, S.1
Kott, S.R.S.S.2
Xu, X.3
Canno, J.F.4
Headley, A.D.5
Li, G.6
-
10
-
-
34250618403
-
-
(d) Han, J. L.; Zhi, S. J.; Wang, L. Y.; Pan, Y.; Li, G. Eur. J. Org. Chem. 2007, 1332-1337.
-
(2007)
Eur. J. Org. Chem.
, pp. 1332-1337
-
-
Han, J.L.1
Zhi, S.J.2
Wang, L.Y.3
Pan, Y.4
Li, G.5
-
11
-
-
37249018997
-
-
(a) Rawal, G. K.; Kumar, A.; Tawar, U.; Vankar, Y. D. Org. Lett. 2007, 9, 5171-5174.
-
(2007)
Org. Lett.
, vol.9
, pp. 5171-5174
-
-
Rawal, G.K.1
Kumar, A.2
Tawar, U.3
Vankar, Y.D.4
-
12
-
-
0033588364
-
-
(b) Kirschning, A.; Hashem, M. D.; Monenschein, H.; Rose, L.; Schonng, K. U. J. Org. Chem. 1999, 64, 6522-6526.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 6522-6526
-
-
Kirschning, A.1
Hashem, M.D.2
Monenschein, H.3
Rose, L.4
Schonng, K.U.5
-
13
-
-
0001749012
-
-
(c) Bellucci, G.; Bianchini, R.; Chiappe, C. J. Org. Chem. 1991, 56, 3067-3073.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 3067-3073
-
-
Bellucci, G.1
Bianchini, R.2
Chiappe, C.3
-
15
-
-
33646491913
-
-
(e) Wang, Z. G.; Warren, J. D.; Dudkin, V. Y.; Zhang, X.; Iserloh, U.; Visser, M.; Eckhardt, M.; Seeberger, P. H.; Danishefsky, S. J. Tetrahedron 2006, 62, 4954-4978.
-
(2006)
Tetrahedron
, vol.62
, pp. 4954-4978
-
-
Wang, Z.G.1
Warren, J.D.2
Dudkin, V.Y.3
Zhang, X.4
Iserloh, U.5
Visser, M.6
Eckhardt, M.7
Seeberger, P.H.8
Danishefsky, S.J.9
-
17
-
-
0034670616
-
-
(g) Boschi, A.; Chiappe, C.; De Rubertis, A.; Russe, M. F. J. Org. Chem. 2000, 65, 8470-8477.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 8470-8477
-
-
Boschi, A.1
Chiappe, C.2
De Rubertis, A.3
Russe, M.F.4
-
19
-
-
0035936677
-
-
(i) Owens, J. M.; Yung, B. K. S.; Hill, D. C.; Petillo, P. A. J. Org. Chem. 2001, 66, 1484-1486.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 1484-1486
-
-
Owens, J.M.1
Yung, B.K.S.2
Hill, D.C.3
Petillo, P.A.4
-
20
-
-
0035835041
-
-
(j) Kim, H. M.; Kim, J. J.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 35-48.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 35-48
-
-
Kim, H.M.1
Kim, J.J.2
Danishefsky, S.J.3
-
21
-
-
17744386349
-
-
(k) Spassova, M. K.; Bornmann, W. G.; Ragupathi, G.; Sukenick, G.; Livingston, P. O.; Danishefsky, S. J. J. Org. Chem. 2005, 70, 3383-3395.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 3383-3395
-
-
Spassova, M.K.1
Bornmann, W.G.2
Ragupathi, G.3
Sukenick, G.4
Livingston, P.O.5
Danishefsky, S.J.6
-
22
-
-
0347991622
-
-
(l) Garcia, J. I.; Mateo, F. H.; Flores, F. G. C.; Gonzalez, F. S. J. Org. Chem. 2004, 69, 202-205.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 202-205
-
-
Garcia, J.I.1
Mateo, F.H.2
Flores, F.G.C.3
Gonzalez, F.S.4
-
23
-
-
0034987043
-
-
(m) Raghavan, S.; Reddy, S. R.; Tony, K. A.; Kumar, C. N.; Nanda, S. Synlett 2001, 851-853.
-
(2001)
Synlett
, pp. 851-853
-
-
Raghavan, S.1
Reddy, S.R.2
Tony, K.A.3
Kumar, C.N.4
Nanda, S.5
-
25
-
-
33746588233
-
-
(o) Yeung, Y. Y.; Gau, X.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 9644-9645.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 9644-9645
-
-
Yeung, Y.Y.1
Gau, X.2
Corey, E.J.3
-
26
-
-
11844262714
-
-
(p) Nyffeler, P. T.; Duron, S. G.; Burkart, M. D.; Vincet, S. P.; Wong, C. H. Angew. Chem., Int. Ed. 2005, 44, 192-212.
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 192-212
-
-
Nyffeler, P.T.1
Duron, S.G.2
Burkart, M.D.3
Vincet, S.P.4
Wong, C.H.5
-
27
-
-
4444276560
-
-
Raghavan, S.; Naveen Kumar, Ch.; Tony, K. A.; Ramakrishna Reddy, S.; Ravikumar, K. Tetrahedron Lett. 2004, 45, 7231-7234.
-
(2004)
Tetrahedron Lett.
, vol.45
, pp. 7231-7234
-
-
Raghavan, S.1
Naveen Kumar, Ch.2
Tony, K.A.3
Ramakrishna Reddy, S.4
Ravikumar, K.5
-
28
-
-
67249089453
-
-
note
-
The cis-alkenes were obtained in nine steps from cis-2-butene-1,4-diol as depicted below. (Chemical Equation Presented)
-
-
-
-
30
-
-
44249103452
-
-
(a) Raghavan, S.; Mustafa, S.; Rathore, K. Tetrahedron Lett. 2008, 49, 4256-4259.
-
(2008)
Tetrahedron Lett.
, vol.49
, pp. 4256-4259
-
-
Raghavan, S.1
Mustafa, S.2
Rathore, K.3
-
32
-
-
0342621309
-
-
The β-hydroxy γ,δ-cis-alkenes cannot be derived from the reaction of cis esters with the lithio anion of aryl methyl sulfoxide followed by reduction of the resulting β-keto sulfoxides since the cis ester undergoes isomerization to the trans ester. The alternative reaction of acetylenic esters with lithio anion of aryl methyl sulfoxide followed by reduction of the resulting ynones suffers from poor stereoselectivity; see
-
The β-hydroxy γ,δ-cis-alkenes cannot be derived from the reaction of cis esters with the lithio anion of aryl methyl sulfoxide followed by reduction of the resulting β-keto sulfoxides since the cis ester undergoes isomerization to the trans ester. The alternative reaction of acetylenic esters with lithio anion of aryl methyl sulfoxide followed by reduction of the resulting ynones suffers from poor stereoselectivity; see: Sanchez-Obregon, R.; Ortiz, B.; Walls, F.; Yuste, F.; Garcia Ruano, J. L. Tetrahedron: Asymmetry 1999, 10, 947-955.
-
(1999)
Tetrahedron: Asymmetry
, vol.10
, pp. 947-955
-
-
Sanchez-Obregon, R.1
Ortiz, B.2
Walls, F.3
Yuste, F.4
Garcia Ruano, J.L.5
-
33
-
-
1842681980
-
-
Gao, G.; Xie, R.-G.; Pu, L. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5417-5420.
-
(2004)
Proc. Natl. Acad. Sci. U.S.A.
, vol.101
, pp. 5417-5420
-
-
Gao, G.1
Xie, R.-G.2
Pu, L.3
-
34
-
-
67249136004
-
-
note
-
p-Tolylthio acetaldehyde was obtained by IBX oxidation of p-tolylthio ethanol.
-
-
-
-
35
-
-
67249096044
-
-
note
-
In future, with an efficient catalyst becoming available for the preparation of propargylic alcohols, by the direct reaction of aldehydes and alkynes, we can prepare optically active sulfilimines with excellent enantioselectivity readily in only three steps.
-
-
-
-
36
-
-
0029836898
-
-
For other alternative approaches to the reduction of ynones, see
-
For other alternative approaches to the reduction of ynones, see: (a) Helal, C. J.; Magriotis, P. A.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 10938-11939
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 10938-11939
-
-
Helal, C.J.1
Magriotis, P.A.2
Corey, E.J.3
-
37
-
-
0037084327
-
-
(b) Schubert, T.; Hummel, W.; Müller, M. Angew. Chem., Int. Ed. 2002, 41, 634-637.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 634-637
-
-
Schubert, T.1
Hummel, W.2
Müller, M.3
-
38
-
-
33947621641
-
-
Choudhary, A.; Breslav, M.; Grimm, J. S.; Xiao, T.; Xu, D.; Sorgi, K. L. Tetrahedron Lett. 2007, 48, 3069-3072.
-
(2007)
Tetrahedron Lett.
, vol.48
, pp. 3069-3072
-
-
Choudhary, A.1
Breslav, M.2
Grimm, J.S.3
Xiao, T.4
Xu, D.5
Sorgi, K.L.6
-
39
-
-
0033546106
-
-
Devocelle, M.; Mortreux, A.; Agbossou, F.; Dormoy, J.-P. Tetrahedron Lett. 1999, 40, 4551-4554.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 4551-4554
-
-
Devocelle, M.1
Mortreux, A.2
Agbossou, F.3
Dormoy, J.-P.4
-
40
-
-
3342948477
-
-
Hamada, T.; Torii, T.; Izawa, K.; Ikariya, T. Tetrahedron 2004, 60, 7411-7417.
-
(2004)
Tetrahedron
, vol.60
, pp. 7411-7417
-
-
Hamada, T.1
Torii, T.2
Izawa, K.3
Ikariya, T.4
-
41
-
-
0001040853
-
-
(a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562-7563.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 7562-7563
-
-
Hashiguchi, S.1
Fujii, A.2
Takehara, J.3
Ikariya, T.4
Noyori, R.5
-
42
-
-
0029879373
-
-
(b) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 2521-2522
-
-
Fujii, A.1
Hashiguchi, S.2
Uematsu, N.3
Ikariya, T.4
Noyori, R.5
-
43
-
-
0030984352
-
-
(c) Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1997, 36, 285-288.
-
(1997)
Angew. Chem., Int. Ed.
, vol.36
, pp. 285-288
-
-
Haack, K.-J.1
Hashiguchi, S.2
Fujii, A.3
Ikariya, T.4
Noyori, R.5
-
44
-
-
0030984556
-
-
(d) Hashiguchi, S.; Fujii, A.; Haack, K.-J.; Matsumura, K.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1997, 36, 288-290.
-
(1997)
Angew. Chem., Int. Ed.
, vol.36
, pp. 288-290
-
-
Hashiguchi, S.1
Fujii, A.2
Haack, K.-J.3
Matsumura, K.4
Ikariya, T.5
Noyori, R.6
-
45
-
-
0030883527
-
-
(e) Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738-8739.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 8738-8739
-
-
Matsumura, K.1
Hashiguchi, S.2
Ikariya, T.3
Noyori, R.4
-
47
-
-
67249161000
-
-
note
-
The enantioselectivity was determined by chiral HPLC; see the Supporting Information. The S configuration was assigned on the basis of literature precedent.
-
-
-
-
48
-
-
67249113344
-
-
note
-
The hydrogenation in EtOAc as the solvent afforded the alcohol in poor yield. The substrate to catalyst ratio (25:1) was found to be optimal. With a higher substrate to catalyst ratio (100:1) side reactions were observed.
-
-
-
-
49
-
-
0027095997
-
-
(a) Takahashi, A.; Endo, T.; Nozoe, S. Chem. Pharm. Bull. 1992, 40, 3181-3184.
-
(1992)
Chem. Pharm. Bull.
, vol.40
, pp. 3181-3184
-
-
Takahashi, A.1
Endo, T.2
Nozoe, S.3
-
54
-
-
0025965421
-
-
(f) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. Tetrahedron 1991, 47, 1677-1696.
-
(1991)
Tetrahedron
, vol.47
, pp. 1677-1696
-
-
Alexakis, A.1
Marek, I.2
Mangeney, P.3
Normant, J.F.4
-
58
-
-
67249154290
-
-
note
-
1H NMR to the corresponding N-Ts-sulfilimines.
-
-
-
-
59
-
-
61349127170
-
-
and references cited therein
-
Collet, F.; Dodd, R. H.; Dauban, P. Org. Lett. 2008, 10, 5473-5476, and references cited therein.
-
(2008)
Org. Lett.
, vol.10
, pp. 5473-5476
-
-
Collet, F.1
Dodd, R.H.2
Dauban, P.3
-
60
-
-
33748542524
-
-
For reviews of the effects of 1,3-allylic strain on conformation and stereoselectivity, see
-
For reviews of the effects of 1,3-allylic strain on conformation and stereoselectivity, see: (a) Johnson, F. Chem. Rev. 1968, 68, 375-413.
-
(1968)
Chem. Rev.
, vol.68
, pp. 375-413
-
-
Johnson, F.1
-
62
-
-
0003536850
-
-
Baldwin, J. E., Ed.; Pergamon Press: New York
-
Deslongchamps, P. In Stereoelctronic Effects in Organic Chemistry, 1st ed.; Baldwin, J. E., Ed.; Pergamon Press: New York, 1983; Vol.1.
-
(1983)
Stereoelctronic Effects in Organic Chemistry, 1st Ed.
, vol.1
-
-
Deslongchamps, P.1
-
63
-
-
0035966209
-
-
Guindon, Y.; Soucy, F.; Yaokim, C.; Ogilvie, W. W.; Plamondon, L. J. Org. Chem. 2001, 66, 8992-8996.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 8992-8996
-
-
Guindon, Y.1
Soucy, F.2
Yaokim, C.3
Ogilvie, W.W.4
Plamondon, L.5
-
64
-
-
0021955975
-
-
Danishefsky, S. J.; Larson, E.; Springer, J. P. J. Am. Chem. Soc. 1985, 107, 1274-1280.
-
(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 1274-1280
-
-
Danishefsky, S.J.1
Larson, E.2
Springer, J.P.3
-
65
-
-
67249156934
-
-
Houk, K. N.; Moses, S. R.; Wu, Y.-D.; Rondan, N. G.; Jager, V.; Schohe, R.; Froncek, F. R. J. Am. Chem. Soc. 1987, 109, 650-663.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 650-663
-
-
Houk, K.N.1
Moses, S.R.2
Wu, Y.-D.3
Rondan, N.G.4
Jager, V.5
Schohe, R.6
Froncek, F.R.7
-
66
-
-
67249092759
-
-
See the Supporting Information
-
See the Supporting Information.
-
-
-
|