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Chemical Communications

Volumn , Issue 25, 2006, Pages 2667-2669

Chemo-differentiating MCRs based on α-ketoesters and terminal alkynoates. A homoaldol-based ABB′ system

(3) Tejedor, David a,b Santos Expósito, Alicia a,b García Tellado, Fernando a,b

a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA (Spain)

b Madrid Spain (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; ESTER; KETONE; TERTIARY AMINE;

ACIDITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; MICHAEL ADDITION; MULTICOMPONENT REACTION; PKA; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 33745192797 PISSN: 13597345 EISSN: None Source Type: Journal
DOI: 10.1039/b605075a Document Type: Article

Times cited : (29)

References (25)

1
- 84890597202
- J. Zhu and H. Bienaymé, Wiley-VCH, Weinheim, Germany
- Multicomponent Reactions, ed., J. Zhu and H. Bienaymé,, Wiley-VCH, Weinheim, Germany, 2005
- (2005) Multicomponent Reactions, Ed.

2
- 31544434530
- A. Dömling Chem. Rev. 2006 106 17 89
- (2006) Chem. Rev. , vol.106 , pp. 17-89
- Dömling, A.¹

3
- 17144366282
- D. J. Ramón M. Yus Angew. Chem., Int. Ed. 2005 44 1602 1634
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 1602-1634
- Ramón, D.J.¹ Yus, M.²

4
- 11144310072
- C. Simon T. Constantieux J. Rodriguez Eur. J. Org. Chem. 2004 4957 4980
- (2004) Eur. J. Org. Chem. , pp. 4957-4980
- Simon, C.¹ Constantieux, T.² Rodriguez, J.³

5
- 0042745386
- R. V. A. Orru M. de Greef Synthesis 2003 10 1471 1499
- (2003) Synthesis , vol.10 , pp. 1471-1499
- Orru, R.V.A.¹ De Greef, M.²

6
- 0141757224
- A. Jacobi von Wangelin H. Neumann D. Gördes S. Klaus D. Strübing M. Beller Chem.-Eur. J. 2003 9 4286 4294
- (2003) Chem.-Eur. J. , vol.9 , pp. 4286-4294
- V.wangelin, J.A.¹ Neumann, H.² Gördes, D.³ Klaus, S.⁴ Strübing, D.⁵ Beller, M.⁶

7
- 0034665244
- H. Bienaymé C. Hulme G. Oddon P. Schmidtt Chem.-Eur. J. 2000 6 3321 3328
- (2000) Chem.-Eur. J. , vol.6 , pp. 3321-3328
- Bienaymé, H.¹ Hulme, C.² Oddon, G.³ Schmidtt, P.⁴

8
- 20444500603
- D. Tejedor D. González-Cruz A. Sántos-Expósito J. J. Marrero-Tellado P. Armas F. García-Tellado Chem.-Eur. J. 2005 11 3502 3510
- (2005) Chem.-Eur. J. , vol.11 , pp. 3502-3510
- Tejedor, D.¹ González-Cruz, D.² Sántos-Expósito, A.³ Marrero-Tellado, J.J.⁴ Armas, P.⁵ García-Tellado, F.⁶

9
- 13244267096
- D. Tejedor A. Sántos-Expósito D. González-Cruz J. J. Marrero-Tellado F. García-Tellado J. Org. Chem. 2005 70 1042 1045
- (2005) J. Org. Chem. , vol.70 , pp. 1042-1045
- Tejedor, D.¹ Sántos-Expósito, A.² González-Cruz, D.³ Marrero-Tellado, J.J.⁴ García-Tellado, F.⁵

10
- 3142724941
- D. Tejedor D. González-Cruz F. García-Tellado J. J. Marrero-Tellado M. López Rodriguez J. Am. Chem. Soc. 2004 126 8390 8391
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 8390-8391
- Tejedor, D.¹ González-Cruz, D.² García-Tellado, F.³ Marrero-Tellado, J.J.⁴ López Rodriguez, M.⁵

11
- 0345381993
- D. Tejedor Aragón G. V. López F. García-Tellado J. J. Marrero-Tellado P. de Armas D. Terrero J. Org. Chem. 2003 68 3363 3365
- (2003) J. Org. Chem. , vol.68 , pp. 3363-3365
- Tejedor Aragón, D.¹ López, G.V.² García-Tellado, F.³ Marrero-Tellado, J.J.⁴ De Armas, P.⁵ Terrero, D.⁶

12
- 0042307518
- D. Tejedor F. García-Tellado J. J. Marrero-Tellado P. de Armas Chem.-Eur. J. 2003 9 3122 3131
- (2003) Chem.-Eur. J. , vol.9 , pp. 3122-3131
- Tejedor, D.¹ García-Tellado, F.² Marrero-Tellado, J.J.³ De Armas, P.⁴

13
- 18044404544
- We have taken this notation from the pioneering work of Powell and Batey:
- P. de Armas F. García-Tellado J. J. Marrero-Tellado D. Tejedor M. A. Maestro J. González-Platas Org. Lett. 2001 3 1905 1908
- (2001) Org. Lett. , vol.3 , pp. 1905-1908
- De Armas, P.¹ García-Tellado, F.² Marrero-Tellado, J.J.³ Tejedor, D.⁴ Maestro, M.A.⁵ González-Platas, J.⁶

14
- 0012815011
- D. A. Powell R. A. Batey Org. Lett. 2002 4 2913 2916
- (2002) Org. Lett. , vol.4 , pp. 2913-2916
- Powell, D.A.¹ Batey, R.A.²

15
- 85083538735
- 2, in which the component B plays the same role twice along the whole process We are preparing a full account of these ABB′ systems with our own contributions and other synthetic examples found in our literature search. For selected examples see:
- 2, in which the component B plays the same role twice along the whole process

16
- 0034804006
- H. Neumann A. J. von Wangelin D. Gördes A. Spannenberg M. Beller J. Am. Chem. Soc. 2001 123 8398 8399
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 8398-8399
- Neumann, H.¹ Von Wangelin, A.J.² Gördes, D.³ Spannenberg, A.⁴ Beller, M.⁵

17
- 0000249975
- H. Shiraishi T. Nishitani S. Sakaguchi Y. Ishii J. Org. Chem. 1998 63 6234 6238
- (1998) J. Org. Chem. , vol.63 , pp. 6234-6238
- Shiraishi, H.¹ Nishitani, T.² Sakaguchi, S.³ Ishii, Y.⁴

18
- 0001547466
- For the synthesis and chemical and biological importance of these heterocycles, see:
- A. J. Kresge P. Pruszynski J. Org. Chem. 1991 56 4808 4811
- (1991) J. Org. Chem. , vol.56 , pp. 4808-4811
- Kresge, A.J.¹ Pruszynski, P.²

19
- 27144479436
- and references cited therein
- R. Dede L. Michaelis P. Langer Tetrahedron Lett. 2005 46 8129 8131
- (2005) Tetrahedron Lett. , vol.46 , pp. 8129-8131
- Dede, R.¹ Michaelis, L.² Langer, P.³

20
- 0031976717
- and references cited therein For other recent synthetic approaches to these structures, see:
- D. Enders H. Dyker F. R. Leusink Chem.-Eur. J. 1998 4 311 320
- (1998) Chem.-Eur. J. , vol.4 , pp. 311-320
- Enders, D.¹ Dyker, H.² Leusink, F.R.³

21
- 27144545042
- P. Dambruoso A. Massi A. Dondoni Org. Lett. 2005 7 4657 4660
- (2005) Org. Lett. , vol.7 , pp. 4657-4660
- Dambruoso, P.¹ Massi, A.² Dondoni, A.³

22
- 3142694085
- M. F. Braña M. L. García B. López B. de Pascual-Teresa A. Ramos J. M. Pozuelo M. T. Domínguez Org. Biomol. Chem. 2004 2 1864 1871
- (2004) Org. Biomol. Chem. , vol.2 , pp. 1864-1871
- Braña, M.F.¹ García, M.L.² López, B.³ De Pascual-Teresa, B.⁴ Ramos, A.⁵ Pozuelo, J.M.⁶ Domínguez, M.T.⁷

23
- 0027323573
- J. Bigorra J. Font C. Ochoa de Echaguen R. M. Ortuño Tetrahedron 1993 49 6717 28
- (1993) Tetrahedron , vol.49 , pp. 6717-6728
- Bigorra, J.¹ Font, J.² D.echaguen, O.C.³ Ortuño, R.M.⁴

24
- 2342571348
- A referee has suggested that the homoaldolic reaction could be catalyzed by triethylamine and not by the allenolate intermediate I. Stirring ethyl pyruvate with a catalytic amount of triethylamine for 48 h at room temperature generates the homoaldol adduct in less than 30% yield. 11 This experimental observation confirms that alkyl propiolate is needed to generate the enolate intermediate III and also to drive the entire process irreversibly toward the isotetronic acid formation For a recent study of catalyzed asymmetric aldol reactions of pyruvates, see:
- M. Kijima K. Miyamori T. Sato J. Org. Chem. 1988 53 1719 172
- (1988) J. Org. Chem. , vol.53 , pp. 1719-1172
- Kijima, M.¹ Miyamori, K.² Sato, T.³

25
- 2342646154
- and references cited therein. In this study, the authors also find that amines are not suitable catalysts for the homoaldol reaction of ethylpyruvate. A copper(ii) complex (metallic catalyst) is essential for the formation of the enol-form and reaction to the homoaldol product For a complete description of these alkynylide-driven domino processes see ref. 3. Note that the reaction network previous to the lactonization step comprises sequential reversible reactions; that means that early intermediates are in equilibrium with starting materials. If lactonization is fast, then the whole process is irreversible and driven to completion; in comparison, if lactonization is slow, the cycle is kinetically blocked and the enolate triggers a new domino process via formation of a conjugated alkynylide anion
- N. Gathergood K. Juhl T. B. Poulse K. Thordrup K. A. Jørgensen Org. Biomol. Chem. 2004 2 1077 1085
- (2004) Org. Biomol. Chem. , vol.2 , pp. 1077-1085
- Gathergood, N.¹ Juhl, K.² Poulse, T.B.³ Thordrup, K.⁴ Jørgensen, K.A.⁵

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