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1
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0003417469
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Trost B.M., and Fleming I. (Eds), Pergamon, Oxford
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In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, Oxford
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(1991)
Comprehensive Organic Synthesis
, vol.2
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2
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11844259698
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Mahrwald R. (Ed), Wiley-VCH, Weinheim
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In: Mahrwald R. (Ed). Modern Aldol Reactions (2004), Wiley-VCH, Weinheim
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(2004)
Modern Aldol Reactions
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-
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4
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34447567998
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For reviews on direct aldol and Mannich(-type) reactions using ketone or aldehyde as pronucleophile, see:
-
-
-
-
10
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-
34447563423
-
-
For selected leading references of direct aldol reactions catalyzed by metal complex, see:
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-
-
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11
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0033526380
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Yoshikawa N., Yamada Y.M.A., Das J., Sasai H., and Shibasaki M. J. Am. Chem. Soc. 121 (1999) 4168
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(1999)
J. Am. Chem. Soc.
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, pp. 4168
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Yoshikawa, N.1
Yamada, Y.M.A.2
Das, J.3
Sasai, H.4
Shibasaki, M.5
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14
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34447535005
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-
For reading references of direct aldol reactions with organocatalyst, see:
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-
-
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21
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11844253794
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-
Cobb A.J.A., Shaw D.M., Longbottom D.A., Gold J.B., and Ley S.V. Org. Biomol. Chem. 3 (2005) 84
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(2005)
Org. Biomol. Chem.
, vol.3
, pp. 84
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Cobb, A.J.A.1
Shaw, D.M.2
Longbottom, D.A.3
Gold, J.B.4
Ley, S.V.5
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23
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34447566716
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-
For N-acyl oxazolidinones or N-acylthiazolidinethiones, see:
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-
-
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27
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-
34447573488
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-
For malonic acid half-thioesters, see:
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-
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29
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19744363827
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Magdziak D., Lalic G., Lee H.M., Fortner K.C., Aloise A.D., and Shair M.D. J. Am. Chem. Soc. 127 (2005) 7284
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J. Am. Chem. Soc.
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Magdziak, D.1
Lalic, G.2
Lee, H.M.3
Fortner, K.C.4
Aloise, A.D.5
Shair, M.D.6
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30
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-
34447572432
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-
For N-acyl pyrroles, see:
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-
-
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31
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22744453251
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Harada S., Handa S., Matsunaga S., and Shibasaki M. Angew. Chem., Int. Ed. 44 (2005) 4365
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(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 4365
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Harada, S.1
Handa, S.2
Matsunaga, S.3
Shibasaki, M.4
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32
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-
34447556478
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-
For trichloromethyl ketones, see:
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-
-
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33
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-
33746255430
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-
Morimoto H., Wiedemann S.H., Yamaguchi A., Harada S., Chen Z., Matsunaga S., and Shibasaki M. Angew. Chem., Int. Ed. 45 (2006) 3146
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(2006)
Angew. Chem., Int. Ed.
, vol.45
, pp. 3146
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Morimoto, H.1
Wiedemann, S.H.2
Yamaguchi, A.3
Harada, S.4
Chen, Z.5
Matsunaga, S.6
Shibasaki, M.7
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34
-
-
34447546375
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-
For N-acyl Boc-amides, see:
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-
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37
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-
34447571451
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For reviews, see:
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-
-
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42
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-
34447555451
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In DMSO, see:
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-
-
-
44
-
-
34447555450
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-
2O, see:
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-
-
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47
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0000115729
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Yamamoto Y., Kubota Y., Honda Y., Fukui H., Asao N., and Nemoto H. J. Am. Chem. Soc. 116 (1994) 3161
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J. Am. Chem. Soc.
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, pp. 3161
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Yamamoto, Y.1
Kubota, Y.2
Honda, Y.3
Fukui, H.4
Asao, N.5
Nemoto, H.6
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53
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0043269708
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Takaya H., Yoshida K., Isozaki K., Terai H., and Murahashi S.-I. Angew. Chem., Int. Ed. 42 (2003) 3302
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(2003)
Angew. Chem., Int. Ed.
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, pp. 3302
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Takaya, H.1
Yoshida, K.2
Isozaki, K.3
Terai, H.4
Murahashi, S.-I.5
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54
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2442531710
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Motokura K., Nishimura D., Mori K., Mizugaki T., Ebitani K., and Kaneda K. J. Am. Chem. Soc. 126 (2004) 5662
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J. Am. Chem. Soc.
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Motokura, K.1
Nishimura, D.2
Mori, K.3
Mizugaki, T.4
Ebitani, K.5
Kaneda, K.6
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61
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34447574473
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For a review:
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-
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63
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34447561410
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tBu:
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-
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64
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0141631816
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Suto Y., Kumagai N., Matsunaga S., Kanai M., and Shibasaki M. Org. Lett. 5 (2003) 3147
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(2003)
Org. Lett.
, vol.5
, pp. 3147
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Suto, Y.1
Kumagai, N.2
Matsunaga, S.3
Kanai, M.4
Shibasaki, M.5
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66
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34447535004
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tOBu:
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-
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71
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34447570383
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For reviews, see:
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74
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34447573487
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Nucleophilic activation of nitrile with stoichiometric amount of Lewis acid, see:
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-
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79
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34447564695
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-
Examples for C-CN bond activation, see:
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-
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83
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34447567997
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For general reviews of CpRu complex, see:
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-
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85
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0001590841
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Slugovc C., Rüba E., Schmid R., Kirchner K., and Mereiter K. Monatsh. Chem. 131 (2000) 1241
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(2000)
Monatsh. Chem.
, vol.131
, pp. 1241
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-
Slugovc, C.1
Rüba, E.2
Schmid, R.3
Kirchner, K.4
Mereiter, K.5
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86
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34447580704
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For preparation of 3a, see:
-
-
-
-
90
-
-
34447578433
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-
note
-
DBN was used as base. DBN proved to be effective with 3b whereas yield was slightly worse than that obtained with DBU.
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-
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91
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0000476716
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Blanchette M.A., Choy W., Davis J.T., Essenfeld A.P., Masamune S., Roush W.R., and Sakai T. Tetrahedron Lett. 25 (1984) 2183
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(1984)
Tetrahedron Lett.
, vol.25
, pp. 2183
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-
Blanchette, M.A.1
Choy, W.2
Davis, J.T.3
Essenfeld, A.P.4
Masamune, S.5
Roush, W.R.6
Sakai, T.7
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92
-
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34447552187
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-
Using bromoacetonitrile, see:
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-
-
-
94
-
-
34447541855
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-
Using trimethylsilylacetonitrile, see:
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-
-
-
99
-
-
23844530814
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-
Mita T., Fujimori I., Wada R., Wen J., Kanai M., and Shibasaki M. J. Am. Chem. Soc. 127 (2005) 11252
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(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 11252
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-
Mita, T.1
Fujimori, I.2
Wada, R.3
Wen, J.4
Kanai, M.5
Shibasaki, M.6
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101
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34447564694
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For preparation of N-Dpp-imine, see:
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-
-
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103
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34447553141
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For a review of general use of N-Dpp-imine in organic synthesis, see:
-
-
-
-
105
-
-
34447548361
-
-
note
-
See Supplementary data.
-
-
-
-
106
-
-
34447562396
-
-
note
-
Ab initio calculation shows a substantial portion of the negative charge resides at the carbon atom in α-cyano carbanions, suggesting that metalated acetonitrile is less likely in the tautomeric ketenimide form (Ref. 6b). See also Ref. 5c.
-
-
-
-
107
-
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34447564693
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-
note
-
Details are summarized in Section 4.
-
-
-
-
108
-
-
34447580703
-
-
note
-
31P NMR analysis.
-
-
-
-
109
-
-
34447541854
-
-
note
-
31P NMR analysis. See also Section 4.
-
-
-
-
110
-
-
6444231446
-
-
Dissociative pathway has been suggested for the ligand exchange of CpRu complex.
-
Dissociative pathway has been suggested for the ligand exchange of CpRu complex. Luginbühl W., Zbinden P., Pittet P.A., Armbruster T., Bürgi B.-H., Merbach A.E., and Ludi A. Inorg. Chem. 30 (1991) 2355
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(1991)
Inorg. Chem.
, vol.30
, pp. 2355
-
-
Luginbühl, W.1
Zbinden, P.2
Pittet, P.A.3
Armbruster, T.4
Bürgi, B.-H.5
Merbach, A.E.6
Ludi, A.7
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112
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34447568976
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Toy, P. H.; Janda, K. D. Abstracts, 219th ACS national meeting, San Francisco, 2000, ORGN-432.
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-
-
-
113
-
-
34447536034
-
-
note
-
*Ru complex exhibited inferior performance in the reaction with 1a.
-
-
-
-
114
-
-
34447566715
-
-
note
-
6 resulted in the worse result.
-
-
-
-
115
-
-
34447533987
-
-
note
-
Trace amounts of dehydrated product are observed occasionally.
-
-
-
-
118
-
-
34447554204
-
-
note
-
The addition to acetone and cyclohexanone derivative was reported in Ref. 10a using strongly basic proazaphosphatrane base.
-
-
-
-
119
-
-
34447561409
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For reviews, see:
-
-
-
-
123
-
-
34447573485
-
-
note
-
6.
-
-
-
-
124
-
-
34447553140
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-
note
-
For an example of catalytic cyanomethylation of trifluoroacetophenone (11a) with trimethylsilylacetonitrile, see Ref. 32b.
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