-
2
-
-
1542429855
-
-
Eliel E.L., and Wilen S.H. (Eds), Wiley, New York, NY pp 124-170
-
Oare D.A., and Heathcock C.A. In: Eliel E.L., and Wilen S.H. (Eds). Topics in Stereochemistry Vol. 20 (1991), Wiley, New York, NY pp 124-170
-
(1991)
Topics in Stereochemistry
, vol.20
-
-
Oare, D.A.1
Heathcock, C.A.2
-
3
-
-
55749109569
-
-
Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds), Springer, New York, NY Chapter 31
-
In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis (1999), Springer, New York, NY Chapter 31
-
(1999)
Comprehensive Asymmetric Catalysis
-
-
-
5
-
-
55749089000
-
-
For comprehensive review articles on the chemo- and regiochemical issues and notable applications of the vinylogous aldol-type chemistry, see:
-
For comprehensive review articles on the chemo- and regiochemical issues and notable applications of the vinylogous aldol-type chemistry, see:
-
-
-
-
15
-
-
55749112358
-
-
In similar reactions involving 2-(trimethylsilyloxy)furans and 3-alkenoyl-1,3-oxazolidin-2-ones, good to excellent diastereo- and enantioselectivity were obtained, by exploiting pyridine bis(oxazoline) (pybox)-lanthanide complexes or binaphthyldiimine-Ni(II) complexes:
-
In similar reactions involving 2-(trimethylsilyloxy)furans and 3-alkenoyl-1,3-oxazolidin-2-ones, good to excellent diastereo- and enantioselectivity were obtained, by exploiting pyridine bis(oxazoline) (pybox)-lanthanide complexes or binaphthyldiimine-Ni(II) complexes:
-
-
-
-
16
-
-
0035905168
-
-
Desimoni G., Faita G., Filippone S., Mella M., Zampori M.G., and Zema M. Tetrahedron 57 (2001) 10203-10212
-
(2001)
Tetrahedron
, vol.57
, pp. 10203-10212
-
-
Desimoni, G.1
Faita, G.2
Filippone, S.3
Mella, M.4
Zampori, M.G.5
Zema, M.6
-
19
-
-
33644780700
-
-
This reaction was also exploited during the enantioselective synthesis of (+)-compactin; here, a crucial role played by the unsaturated aldehyde acceptor was highlighted in guiding the overall stereoselection of the organocatalyzed process:
-
This reaction was also exploited during the enantioselective synthesis of (+)-compactin; here, a crucial role played by the unsaturated aldehyde acceptor was highlighted in guiding the overall stereoselection of the organocatalyzed process:. Robichaud J., and Trembaly F. Org. Lett. 8 (2006) 597-600
-
(2006)
Org. Lett.
, vol.8
, pp. 597-600
-
-
Robichaud, J.1
Trembaly, F.2
-
20
-
-
55749103105
-
-
For examples of 'indirect' VMMAR, see:
-
For examples of 'indirect' VMMAR, see:
-
-
-
-
22
-
-
0037047514
-
-
Arroyo Y., de Paz M., Rodríguez J.F., Sanz-Tejedor M.A., and García Ruano J.L. J. Org. Chem. 67 (2002) 5638-5643
-
(2002)
J. Org. Chem.
, vol.67
, pp. 5638-5643
-
-
Arroyo, Y.1
de Paz, M.2
Rodríguez, J.F.3
Sanz-Tejedor, M.A.4
García Ruano, J.L.5
-
24
-
-
27144551725
-
-
Barluenga J., de Prado A., Santamaría J., and Tomás M. Angew. Chem., Int. Ed. 44 (2005) 6583-6585
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 6583-6585
-
-
Barluenga, J.1
de Prado, A.2
Santamaría, J.3
Tomás, M.4
-
28
-
-
55749112705
-
-
Recent achievements:
-
Recent achievements:
-
-
-
-
35
-
-
55749113050
-
-
Leading references:
-
Leading references:
-
-
-
-
36
-
-
55749084074
-
-
Koćovský P., and Malkov A.V. (Eds)
-
In: Koćovský P., and Malkov A.V. (Eds). Tetrahedron Symposia-in-Print Number 116. Organocatalysis in Organic Synthesis 62 (2006) 243-502
-
(2006)
Organocatalysis in Organic Synthesis
, vol.62
, pp. 243-502
-
-
-
39
-
-
48749133072
-
-
García-García P., Ladépêche A., Halder R., and List B. Angew. Chem., Int. Ed. 47 (2008) 4719-4721
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 4719-4721
-
-
García-García, P.1
Ladépêche, A.2
Halder, R.3
List, B.4
-
40
-
-
55749108747
-
-
Recent achievements:
-
Recent achievements:
-
-
-
-
46
-
-
0034613357
-
-
Rassu G., Auzzas L., Pinna L., Battistini L., Zanardi F., Marzocchi L., Acquotti D., and Casiraghi G. J. Org. Chem. 65 (2000) 6307-6318
-
(2000)
J. Org. Chem.
, vol.65
, pp. 6307-6318
-
-
Rassu, G.1
Auzzas, L.2
Pinna, L.3
Battistini, L.4
Zanardi, F.5
Marzocchi, L.6
Acquotti, D.7
Casiraghi, G.8
-
47
-
-
0035977220
-
-
Rassu G., Auzzas L., Pinna L., Zambrano V., Battistini L., Zanardi F., Marzocchi L., Acquotti D., and Casiraghi G. J. Org. Chem. 66 (2001) 8070-8075
-
(2001)
J. Org. Chem.
, vol.66
, pp. 8070-8075
-
-
Rassu, G.1
Auzzas, L.2
Pinna, L.3
Zambrano, V.4
Battistini, L.5
Zanardi, F.6
Marzocchi, L.7
Acquotti, D.8
Casiraghi, G.9
-
48
-
-
0036087845
-
-
Zanardi F., Battistini L., Marzocchi L., Acquotti D., Rassu G., Pinna L., Auzzas L., Zambrano V., and Casiraghi G. Eur. J. Org. Chem. (2002) 1956-1964
-
(2002)
Eur. J. Org. Chem.
, pp. 1956-1964
-
-
Zanardi, F.1
Battistini, L.2
Marzocchi, L.3
Acquotti, D.4
Rassu, G.5
Pinna, L.6
Auzzas, L.7
Zambrano, V.8
Casiraghi, G.9
-
49
-
-
0037178533
-
-
Rassu G., Auzzas L., Pinna L., Zambrano V., Zanardi F., Battistini L., Marzocchi L., Acquotti D., and Casiraghi G. J. Org. Chem. 67 (2002) 5338-5342
-
(2002)
J. Org. Chem.
, vol.67
, pp. 5338-5342
-
-
Rassu, G.1
Auzzas, L.2
Pinna, L.3
Zambrano, V.4
Zanardi, F.5
Battistini, L.6
Marzocchi, L.7
Acquotti, D.8
Casiraghi, G.9
-
50
-
-
0037700759
-
-
Rassu G., Auzzas L., Pinna L., Zambrano V., Zanardi F., Battistini L., Gaetani E., Curti C., and Casiraghi G. J. Org. Chem. 68 (2003) 5881-5885
-
(2003)
J. Org. Chem.
, vol.68
, pp. 5881-5885
-
-
Rassu, G.1
Auzzas, L.2
Pinna, L.3
Zambrano, V.4
Zanardi, F.5
Battistini, L.6
Gaetani, E.7
Curti, C.8
Casiraghi, G.9
-
51
-
-
1442348962
-
-
See also:
-
Rassu G., Auzzas L., Zambrano V., Burreddu P., Pinna L., Battistini L., Zanardi F., and Casiraghi G. J. Org. Chem. 69 (2004) 1625-1628 See also:
-
(2004)
J. Org. Chem.
, vol.69
, pp. 1625-1628
-
-
Rassu, G.1
Auzzas, L.2
Zambrano, V.3
Burreddu, P.4
Pinna, L.5
Battistini, L.6
Zanardi, F.7
Casiraghi, G.8
-
52
-
-
77957047686
-
-
Atta-ur-Rahman (Ed), Elsevier Science B.V., Amsterdam pp 449-520
-
Rassu G., Auzzas L., Pinna L., Battistini L., and Curti C. In: Atta-ur-Rahman (Ed). Studies in Natural Products Chemistry. Bioactive Natural Products (Part J) Vol. 29 (2003), Elsevier Science B.V., Amsterdam pp 449-520
-
(2003)
Bioactive Natural Products (Part J)
, vol.29
-
-
Rassu, G.1
Auzzas, L.2
Pinna, L.3
Battistini, L.4
Curti, C.5
-
55
-
-
48249106611
-
-
Curti C., Sartori A., Battistini L., Rassu G., Burreddu P., Zanardi F., and Casiraghi G. J. Org. Chem. 73 (2008) 5446-5451
-
(2008)
J. Org. Chem.
, vol.73
, pp. 5446-5451
-
-
Curti, C.1
Sartori, A.2
Battistini, L.3
Rassu, G.4
Burreddu, P.5
Zanardi, F.6
Casiraghi, G.7
-
56
-
-
55749110778
-
-
note
-
During the reaction course, clear evidence of formation of the N-trimethylsilyl adduct from the starting pyrrolinone was observed (TLC, NMR), which returned N-deprotected pyrrolinone under the slightly acidic quenching conditions.
-
-
-
-
57
-
-
0001246453
-
-
For a comprehensive survey on these topics, see: Noteworthily, the presence of an alkoxy substituent at the C4 position of the ring influences the chemical behavior of the pyrrolinone nucleus, deeply affecting the acidity of the H5-protons, as well as the diverse nucleophilic character at the C3 and C5 carbon atoms. For a comprehensive survey on these topics, see:
-
For a comprehensive survey on these topics, see: Noteworthily, the presence of an alkoxy substituent at the C4 position of the ring influences the chemical behavior of the pyrrolinone nucleus, deeply affecting the acidity of the H5-protons, as well as the diverse nucleophilic character at the C3 and C5 carbon atoms. For a comprehensive survey on these topics, see:. Royles B.J. Chem. Rev. 95 (1995) 1981-2001
-
(1995)
Chem. Rev.
, vol.95
, pp. 1981-2001
-
-
Royles, B.J.1
-
58
-
-
55749109407
-
-
Compounds 1c-1e are known substances, which have been nicely exploited in both alkylation and aldol additions/condensations: Li or Na-dienolates:
-
Compounds 1c-1e are known substances, which have been nicely exploited in both alkylation and aldol additions/condensations: Li or Na-dienolates:
-
-
-
-
62
-
-
34250629941
-
-
Fürstner A., Radkowski K., Peters H., Seidel G., Wirtz C., Mynott R., and Lehmann C.W. Chem.-Eur. J. 13 (2007) 1929-1945
-
(2007)
Chem.-Eur. J.
, vol.13
, pp. 1929-1945
-
-
Fürstner, A.1
Radkowski, K.2
Peters, H.3
Seidel, G.4
Wirtz, C.5
Mynott, R.6
Lehmann, C.W.7
-
65
-
-
55749110067
-
-
For examples of tertiary amine-catalyzed direct aldol reactions, see:
-
For examples of tertiary amine-catalyzed direct aldol reactions, see:
-
-
-
-
68
-
-
55749109068
-
-
note
-
Addition of 1c to cinnamaldehyde was also tested, with exclusive, low-yielding production of the trimethylsilyl-protected carbinol from 1,2-carbonyl addition attack.
-
-
-
-
69
-
-
55749099024
-
-
note
-
According to this line of reasoning, complete lack of reactivity between 1c and Z-configured cyclic acceptor 11 could be attributed to the fact that both possible tight transition state models VII and VIII are sterically encumbered and inherently unfavoured.{A figure is presented}
-
-
-
|