The Vinylogous Aldol Reaction
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1 The Vinylogous Aldol Reaction Reporter: Sixuan Meng Supervisor: Prof. Huang Zanardi, F. et al. Chem. Rev. 2000, 100, 1929 Zanardi, F. et al.. Chem. Rev. 2011, 111, 3076
2 Introduction 2
3 3 Regiochemical Issues kinetic thermodynamic
4 4 Dienolates From Unsaturated Aldehydes and Ketons 1. Prenal metal dienolates 2. γ-silyl strategy (1) Duhamel, L. et al. Tetrahedron Lett. 1998, 39, 7093 (2) Duhamel, P. et al. Tetrahedron Lett, 1998, 39, 8975 (3) Kuwajima, I. et al. J. Am. Chem. Soc. 1989, 111, 8277
5 5 Dienolates From Unsaturated Aldehydes and Ketones 3. ATPH strategy Yamamoto, H. et al. J. Am. Chem. Soc. 1998, 120, 813
6 6 Dienolates From Unsaturated Carboxylic Acids Ronchi, A. et al. J. Am. Chem. Soc. Perkin Trans. 1973, 1, 400
7 7 Dienolates From Unsaturated Carboxylic Acids Kurachi, Y. et al. J. Chem. Soc. Chem. Commum. 1977, 500
8 8 Dienolates From Unsaturated Esters (1) Heathcock, C. H. et al. J. Org. Chem, 1980, 45, 1181 (2) Ikekawa, N. et al. Tetrahedron Lett. 1975, 4135
9 9 Dienolates From Unsaturated Amides and Imides chiral auxiliaries Snieckus, V. et al. J. Org. Chem. 1981, 46, 2029
10 10 Dienolates From β-heterosubstituted α,β-unsaturated Carbonyls and Butenolides Holker, J. S. E. et al. J. Chem. Soc. Chem. Commun. 1979, 81
11 11 Dienolates From β-heterosubstituted α,β-unsaturated Carbonyls and Butenolides Gillman, K. W. et al. Tetrahedron Lett. 1999, 40, 1257
12 Dienolates From β-heterosubstituted α,β-unsaturated Carbonyls and Butenolides 12 Schlessinger, R. H. et al. J. Am. Chem. Soc. 1996, 118, 3301 Schlessinger, R. H. et al. J. Org. Chem. 1996, 61, 3226
13 Diastereoselective and Unselective Processes Indirect, Mukaiyama Type Addition of Sillcon Dienolates 1. Acyclic Sillicon Dienolates Representative members of the acyclic d 4 silyl butadiene family 13
14 Diastereoselective and Unselective Processes Indirect, Mukaiyama Type Addition of Sillcon Dienolates 1. Acyclic Sillicon Dienolates Total Synthesis of (+)-Macquarimicin A 14 Tadano, K.-i. et al. J. Am. Chem. Soc. 2003, 125, Tadano, K.-i. et al. J. Am. Chem. Soc. 2004, 126, 11254
15 Diastereoselective and Unselective Processes Indirect, Mukaiyama Type Addition of Sillcon Dienolates 1. Acyclic Sillicon Dienolates Total synthesis of (-)-Callipeltoside A 15 Evans, D. A. et al. Tetrahedron 2008, 64, 4671
16 Kobayashi, S. et al. J. Am. Chem. Soc. 2004, 126, Diastereoselective and Unselective Processes Indirect, Mukaiyama Type Addition of Sillcon Dienolates 1. Acyclic Sillicon Dienolates VMAR addition with chiral vinylketene silyil N,O-acetal 16
17 Diastereoselective and Unselective Processes Indirect, Mukaiyama Type Addition of Sillcon Dienolates 1. Acyclic Sillicon Dienolates 17 Kobayashi, S. et al. J. Am. Chem. Soc. 2004, 126, 13604
18 Scettri, A. et al. Tetrahedron Lett. 2005, 46, 6141 Kirsch, S. et al. Synlett 2001, 1974 Wischert, R. Tetrahedron Lett. 2006, 47, 9089 Diastereoselective and Unselective Processes Indirect, Mukaiyama Type Addition of Sillcon Dienolates 1. Acyclic Sillicon Dienolates Bronsted acid-promoted VMAR to racemic product 18
19 Diastereoselective and Unselective Processes Indirect, Mukaiyama Type Addition of Sillcon Dienolates 2.Cycic Silicon Dienolates First-generation strategy towards cyclohexane and cyclopentane polyols 19 Casiraghi, G. et al. Mini-Rev. Org. Chem. 2004, 1, 343
20 (1) Casiraghi, G. et al. Eur. J. Org. Chem. 2002, 1956 (2) Casiraghi, G. et al. J. Org. Chem. 2001, 66, 8070 Diastereoselective and Unselective Processes Indirect, Mukaiyama Type Addition of Sillcon Dienolates 2.Cycic Silicon Dienolates Diastereoselective synthesis of 5a-carbapyranose and 4a-carbafuranose 20
21 Diastereoselective and Unselective Processes Indirect, Mukaiyama Type Addition of Sillcon Dienolates 2.Cycic Silicon Dienolates Second-generation strategy to amino acid polyols 21 Casiraghi, G. et al. J. Org. Chem. 2006, 71, 225
22 Diastereoselective and Unselective Processes Indirect, Mukaiyama Type Addition of Sillcon Dienolates 2.Cycic Silicon Dienolates Phenylogous aldol moves during the synthesis of Viridin/Wortmannin models 22 Sessions, E. H. et al. Org. Lett. 2006, 8, 4125 Sessions, E. H. et al. Org. Lett. 2007, 9, 3221
23 Diastereoselective and Unselective Processes Direct Addition of in situ-gerenated Dienolates 23
24 Diastereoselective and Unselective Processes Direct Addition of in situ-gerenated Dienolates Aldolization of α,β-unsaturated carbonyl compounds with aldehydes using ATPH 24 Yamamoto, H. et al. J. Am. Chem. Soc. 2003, 125, 6200 γ-regioselective High Z/E selective
25 Diastereoselective and Unselective Processes Direct Addition of in situ-gerenated Dienolates Application of inter- and intramolecular Yamamoto VAR 25 (1) Marquez, R. et al. Angew. Chem. Int. Ed. 2001, 40, 603 (2) Sammakia, T. et al. Org. Lett. 2007, 9, 2103
26 Diastereoselective and Unselective Processes Direct Addition of in situ-gerenated Dienolates Direct vinylogous nitroaldol (Henry) reaction using nitroisoxazole 26 Suresh, S. et al. Org. Lett. 2007, 9, 2103
27 Diastereoselective and Unselective Processes Direct Addition of in situ-gerenated Dienolates Total synthesis of (+)-Castanospermine featuring a diasteteoselective direct VAR 27 Huang, P.-Q. et al. Tetrahedron Lett. 2008, 49, 383 Huang, P.-Q. et al. Eur. J. 2010, 16, 5755
28 Diastereoselective and Unselective Processes Direct Addition of in situ-gerenated Dienolates Synthesis of (S)-Melodorinol 28 Pouliot, M. et al. Synlett 2007, 219
29 Enantioselective Processes Indirect, Mukaiyama type additions of silicon dienolates 1. Acyclic Silicon Dienolates Repersentative metal-based chiral nonracemic complexes used in catalytic enantioselective VMAR 29
30 Enantioselective Processes Indirect, Mukaiyama type additions of silicon dienolates 1. Acyclic Silicon Dienolates Total synthesis of C1-C22 macrolactone fragment of Leucascandrolide A 30 Carreira, E. M. et al. Angew. Chem. Int. Ed. 2002, 41, 4098
31 Enantioselective Processes Indirect, Mukaiyama type additions of silicon dienolates 1. Acyclic Silicon Dienolates Asymmetric VMAR addition involving Chan diene 31 (1) Scettri, A. et al. Tetrahedron:Asymmetry 20000, 11, 2255 (2) Scettri, A. et al. Tetrahedron:Asymmetry 20001, 12, 959
32 Enantioselective Processes Indirect, Mukaiyama type additions of silicon dienolates 1. Acyclic Silicon Dienolates Optimized enantioselective VMAR in the total synthesis of (-)-auriside A 32 Mackay, A. C. et al. Angew. Chem. Int. Ed. 2005, 44, 1130
33 Enantioselective Processes Indirect, Mukaiyama type additions of silicon dienolates 1. Acyclic Silicon Dienolates 33
34 Enantioselective Processes Indirect, Mukaiyama type additions of silicon dienolates 1. Acyclic Silicon Dienolates Enantioselective synthesis of fragment via VMAR catalyzed by Lewis acidic Copper(Ⅱ)-PyBox complex ent-c 34 Evans, D. A. et al. Angew. Chem. Int. Ed. 2007, 46, 541
35 Enantioselective Processes Indirect, Mukaiyama type additions of silicon dienolates 1. Acyclic Silicon Dienolates Biophosphoramide-catalyzed enantioselective VMAR of easter- or dioxinone-derived silyl dienol ethers 35 (1) Denmark, S. E. et al. J. Am. Chem. Soc. 2003, 125, 7800 (2) Denmark, S. E. et al. J. Am. Chem. Soc. 2005, 127, 3774
36 Enantioselective Processes Indirect, Mukaiyama type additions of silicon dienolates 1. Acyclic Silicon Dienolates Biophosphoramide-catalyzed enantioselective VMAR of ketone-, β- diketone, or amide-derived silyl dieolates 36 Denmark, S. E. et al. J. Am. Chem. Soc. 2005, 127, 8971 Denmark, S. E. et al. J. Org. Chem. 2007, 72, 5668
37 Enantioselective Processes Indirect, Mukaiyama type additions of silicon dienolates 1. Acyclic Silicon Dienolates Use of chiral oxazaborolidine catalysts in asymmetric VMAR 37 Simsek, S. et al. Org. Lett. 2007, 9, 5637
38 Enantioselective Processes Indirect, Mukaiyama type additions of silicon dienolates 1. Acyclic Silicon Dienolates Hydrogen bond-catalyzed asymmetric VMAR of dioxinone and various aldehydes 38 Rawal, V. H. et al. Org. Lett. 2005, 7, 5657
39 Enantioselective Processes Indirect, Mukaiyama type additions of silicon dienolates 2. Cyclic Silicon Dienolates Ti(Oi-Pr) 4 /(R)-BINOL catalyzed VMAR of silyoxy furan 39 Szlosek, M. et al. Heterocycles 2000, 52, 1005 Szlosek, M. et al. Angew. Chem. Int. Ed. 2000, 39, 1799
40 Enantioselective Processes Indirect, Mukaiyama type additions of silicon dienolates 2. Cyclic Silicon Dienolates Enantioselective VMAR using quinine-thiourea catalyst 40 Wang, W. et al. Adv. Synth. Catal. 2010, 352, 1291
41 Shibasaki, M. et al. Tetrahedron Lett. 2006, 47, 1043 Shibasaki, M. et al. J. Am. Chem. Soc. 2007, 129, 7439 Enantioselective Processes Direct addition of in situ-generated dienolates Asymmetric reductive VAR of allenic esters to ketones 41
42 Enantioselective Processes Direct addition of in situ-generated dienolates Asymmetric alkylative VAR of Allenic esters to ketones 42 Shibasaki, M. et al. J. Am. Chem. Soc. 2007, 129, 7439
43 Enantioselective Processes Direct addition of in situ-generated dienolates Synthesis of α-tocopherol highlighting a direct asymmetric VAR using dienamine organocatalysis 43 Liu, K. et al. Angew. Chem. Int. Ed. 2008, 47, 5827
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