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Tomioka, K.1
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4544364626
-
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In terms of substrate generality, the La-O-linked-BINOL complex is the most effective catalyst for the present Michael reaction of malonate, see Ref. 19e,g.
-
In terms of substrate generality, the La-O-linked-BINOL complex is the most effective catalyst for the present Michael reaction of malonate, see Ref. 19e,g.
-
-
-
-
78
-
-
4544330868
-
-
note
-
A industrial-scale reaction (>50 kg) is now under investigation.
-
-
-
-
79
-
-
4544260897
-
-
note
-
Syn-selective aldol reaction of indole compound and following anti-elimination gave moderate selectivity (E/Z=8:1)
-
-
-
-
81
-
-
4544308694
-
-
note
-
Enone formation through phenylselenenylation or allyl carbonate formation resulted in very low yield (<20%).
-
-
-
-
82
-
-
0346541206
-
-
General catalytic Saegusa-Ito reaction was established by Tsuji, see: I. Minami, K. Takahashi, I. Shimizu, T. Kimura, and J. Tsuji Tetrahedron 42 1986 2971 and references therein
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Minami, I.1
Takahashi, K.2
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Tsuji, J.5
-
93
-
-
4544379992
-
-
note
-
Other desilylation reagents such as TBAF and HF·Py gave unsatisfactory results (decomposition and deprotection of PMB group, respectively).
-
-
-
-
94
-
-
4544329990
-
-
note
-
The corresponding allylic chloride and bromide showed very low reactivity as compared with mesylate. Thus, allylic alcohol 22 was first converted to the mesylate using methanesulfonic anhydride, not methanesulfonic chloride, which gave a mixture of allylic mesylate and chloride even at low temperature. The corresponding tosylate, which was prepared using p-toluenesulfonic anhydride, gave lower yield
-
-
-
-
95
-
-
7044235263
-
-
For a general review of domino reaction, see: L.F. Tietze Chem. Rev. 96 1996 115
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-
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Tietze, L.F.1
-
96
-
-
4544256709
-
-
note
-
Aniline derivative 25 did not introduce an amine side-chain due to rapid cyclization of the hydroxyl group after removal of the TIPS group.
-
-
-
-
97
-
-
0025779899
-
-
In contrast, Bonjoch et al. reported that 8-aryl-2-azabicyclo[3.3.1] nonane-7-ones easily underwent a retro-1,4-addition, even using an aniline-type analogue. See: J. Bonjoch, J. Quirante, D. Solé, J. Castells, M. Galceran, and J. Bosch Tetrahedron 47 1991 4417
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Bonjoch, J.1
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-
98
-
-
4544289397
-
-
Although we initially used the term 'tandem cyclization' for the reaction shown in Scheme 9 (Ref. 9), we use herein 'domino cyclization' based on Prof. Tietze's suggestion. See Ref. 34.
-
Although we initially used the term 'tandem cyclization' for the reaction shown in Scheme 9 (Ref. 9), we use herein 'domino cyclization' based on Prof. Tietze's suggestion. See Ref. 34.
-
-
-
-
101
-
-
4544356504
-
-
note
-
17β: 3.0 Hz)
-
-
-
-
102
-
-
0026570662
-
-
Bosch et al. (Ref. 17b) and Magnus et al. also investigated other types of cyclization, see: P. Magnus, N.L. Sear, C.S. Kim, and N. Vicker J. Org. Chem. 57 1992 70
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Magnus, P.1
Sear, N.L.2
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Vicker, N.4
-
104
-
-
85057633710
-
-
3: from 1.29 and 1.24 to 0.97). See Ref. 17b.
-
3: from 1.29 and 1.24 to 0.97). See Ref. 17b.
-
-
-
-
105
-
-
85057633016
-
-
note
-
4.
-
-
-
-
106
-
-
0001336738
-
-
Trost, B. M., Freming, I., Eds.; Pergamon: Oxford Chapter 4.3 and references therein.
-
For a general review of reduction of C-S bond, see: Caubère, P.; Coutrot, P. In Comprehensive Organic Synthesis; Trost, B. M., Freming, I., Eds.; Pergamon: Oxford, 1991; Vol. 8, p 835. Chapter 4.3 and references therein.
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Caubère, P.1
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107
-
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4243746641
-
-
The transformation of strychnine (exo-olefin) to neostrychnine (endo-olefin) using normal Raney Ni in EtOH was reported, see: R.L. Beddoes, A.A. Gorman, and A.L. Prescott Acta Crystallogr. C50 1994 447 and references therein
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Beddoes, R.L.1
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108
-
-
85057633452
-
-
note
-
* interaction.
-
-
-
-
110
-
-
4544290193
-
-
note
-
When EtOH was used as a solvent, the reaction proceeded very fast with low selectivity (62: 64 =∼1:1). On the other hand, MeOH had low reactivity (half conversion even with large reagent excess) and high selectivity (62: 64 =>50:1).
-
-
-
-
111
-
-
0021684854
-
-
M. Nicoletti, M.O.F. Goulart, R. De Lima, A.E. Goulart, F. Delle Monache, and B.G.B. Marini J. Nat. Prod. 47 1984 953
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113
-
-
37049055262
-
-
(c) Transformation of diaboline (65) to Wieland-Gumlich aldehyde (66) was reported although details were not described, see: J.S. Grossert, J.M. Hugo, M.E.V. Klemperer, and F.L. Warren J. Chem. Soc., Abstracts 1965 2812
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Grossert, J.S.1
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114
-
-
4544329411
-
-
The spectroscopic data for synthetic 65 and 1 matched those reported previously, see Section 4.
-
The spectroscopic data for synthetic 65 and 1 matched those reported previously, see Section 4.
-
-
-
-
115
-
-
0035814020
-
-
M. Stockley, W. Clegg, G. Fontana, B.T. Golding, N. Martin, L.J.M. Rigoreau, G.C.M. Smith, and R.J. Griffin Bioorg. Med. Chem. Lett. 11 2001 2837
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116
-
-
0034607725
-
-
2NEt (2.0 equiv), toluene (0.2 M), 80°C for 2 h, 92% yield. For the data, see: D. Li, B. Zhao, and E.J. LaVoie J. Org. Chem. 65 2000 2802
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Li, D.1
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117
-
-
85057633712
-
-
note
-
2, 0°C to rt for 12 h. The obtained product was purified by distillation (76-78°C/4 mm Hg). The two-step yield of amination and domino cyclization was highly dependent on the purity of the thioacetal.
-
-
-
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