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For the formation of 1,5-diionic phosphorous betaines, see: (h)
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22144481646
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Asymmetric synthesis of tertiary carbon centers from alkylidene Meldrum's acids and dialkylzinc reagents: (a)
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Asymmetric synthesis of tertiary carbon centers from alkylidene Meldrum's acids and dialkylzinc reagents: (a) Knöpfel, T. F.; Zarotti, P.; Ichikawa, T.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 9682-9683.
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41149101973
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60
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70449715219
-
-
note
-
The absolute stereochemistry of Meldrum's acid 6 was assigned by derivatization to known compounds; see ref 4d.
-
-
-
-
61
-
-
1942468009
-
-
An interesting observation was made regarding the overall superior electrophilicity of alkylidene Meldrum's acids compared to their structurally similar alkylidene dimethyl malonates. Under conditions in which alkylidene Meldrum's acid 4 is alkylated in > 99%conversion, the analogous alkylidene malonate was inert. For asymmetric 1,4-addition of organozinc or aluminum reagents to alkylidene malonates for the formation of tertiary stereocentres, see: (a)
-
An interesting observation was made regarding the overall superior electrophilicity of alkylidene Meldrum's acids compared to their structurally similar alkylidene dimethyl malonates. Under conditions in which alkylidene Meldrum's acid 4 is alkylated in > 99%conversion, the analogous alkylidene malonate was inert. For asymmetric 1,4-addition of organozinc or aluminum reagents to alkylidene malonates for the formation of tertiary stereocentres, see: (a) Schppan, J.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2004, 792-793.
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Schppan, J.1
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63
-
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70449726563
-
-
note
-
It was necessary that the nitrogen substituent be electron-withdrawing group to prevent decomposition of isolated products. Otherwise, elimination of the heteroaromatic ring generating 1-alkylalkylidenes Meldrum's acid was observed.
-
-
-
-
64
-
-
70449720630
-
-
note
-
The absolute stereochemistry of 67 was assigned by X-ray crystallography; see the Supporting Information.
-
-
-
-
65
-
-
70449710858
-
-
note
-
Despite higher catalysts loading, a low 59% conversion was observed.
-
-
-
-
66
-
-
70449701542
-
-
note
-
The analogous cyclohexyl derivative was also unreactive toward conjugate addition of Et2Zn.
-
-
-
-
67
-
-
70449710857
-
-
note
-
For the addition of Me2Zn, the 2-naphthyl derivative of ligand 5 was used.
-
-
-
-
68
-
-
54049148627
-
-
Catalytic asymmetric synthesis of 1,1-disubstituted indanes: (a)
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Catalytic asymmetric synthesis of 1,1-disubstituted indanes: (a) García-Fortanet, J.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 8108-8111.
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García-Fortanet, J.1
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23044496800
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Catalytic asymmetric synthesis of 1-substituted indans: (b)
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Catalytic asymmetric synthesis of 1-substituted indans: (b) Arp, F. O.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 10482-10483.
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(c) Troutman, M. V.; Apella, D. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4916-4917.
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23744457091
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For reviews on the synthesis of indans, see: (d)
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For reviews on the synthesis of indans, see: (d) Ferraz, H. M. C.; Aguilar, A. M.; Silva, L. F., Jr; Craveiro, M. V. Quim. Nova 2005, 28, 703-712.
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Ferraz, H.M.C.1
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73
-
-
70449717004
-
-
note
-
The absolute stereochemistry of 106 was assigned by X-ray crystallography; see the Supporting Information.
-
-
-
-
74
-
-
70449705958
-
-
note
-
See page 2809 in ref 1d.
-
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-
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75
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33749234969
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Zhang, H.; Gschwind, R. M. Angew. Chem., Int. Ed. 2006, 45, 6391-6394.
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Zhang, H.1
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76
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64149093482
-
-
This is consistent with published crystallographic data for alkylidene Meldrum's acids. (a) For a recent discussion on Meldrum's acid's boat conformation, see
-
This is consistent with published crystallographic data for alkylidene Meldrum's acids. (a) For a recent discussion on Meldrum's acid's boat conformation, see: Chopra, D.; Zhurov, V. V.; Zhurova, E. A.; Pinkerton, A. A. J. Org. Chem. 2009, 74, 2389-2395.
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77
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70449713376
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-
For the crystal structure of 5-(benzyl)-2,2-dimethyl-1,3-dioxane-4,6- dione (monosubstituted alkylidene), see
-
(b) For the crystal structure of 5-(benzyl)-2,2-dimethyl-1,3-dioxane-4,6- dione (monosubstituted alkylidene), see: Dong, N.; Cai, G.-Q.; Wu, N.-C.; Huang, X.; Hu, S.-Z.; Chen, M.-D.; Mak, T. C.WChin. Sci. Bull. 1989, 34, 1955-1960.
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78
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0000705231
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For a review on the conformation of alkylidene Meldrum's acids and similar derivatives, see
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(c) For a review on the conformation of alkylidene Meldrum's acids and similar derivatives, see: Sato, M.; Sunami, S.; Kaneko, C. Heterocycles 1996, 42, 861-883.
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70449729456
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For a discussion of benzyl Meldrum's acid conformation, see
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(d) For a discussion of benzyl Meldrum's acid conformation, see: Shengzhi, H. J. Struct. Chem. 1985, 4, 107-114.
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(1985)
J. Struct. Chem.
, vol.4
, pp. 107-114
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Shengzhi, H.1
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80
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37049099279
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Original structure determination by X-ray crystallography
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(e) Original structure determination by X-ray crystallography: Pfluger, C. E.; Boyle, P. D. J. Chem. Soc., Perkin Trans. 2 1985, 1547-1549.
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(1985)
J. Chem. Soc., Perkin Trans. 2
, pp. 1547-1549
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-
Pfluger, C.E.1
Boyle, P.D.2
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81
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70449703341
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note
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The unit cell contains two molecules, thus two sets of data. The dihedral angle C(27)-C(33)-C(34)-C(39) for the second molecule is -100.4°. Bond length C(27)-C(33) is 1.35 Å.
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82
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0028850174
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An example of atropoisomerism with alkylidene Meldrum's acid was reported; see
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An example of atropoisomerism with alkylidene Meldrum's acid was reported; see: Huck, N. P. M.; Meetsma, A.; Zijlstra, R.; Feringa, B. L. Tetrahedron Lett. 1995, 36, 9381-9384.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 9381-9384
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Huck, N.P.M.1
Meetsma, A.2
Zijlstra, R.3
Feringa, B.L.4
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85
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64549130886
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2-H(7-position). A persistent, intramolecular C-H⋯X (X = O, S, Br, Cl, and F) hydrogen bond in solution and solid states was previously reported for benzyl Meldrum's acid derivatives; see
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2-H(7-position). A persistent, intramolecular C-H⋯X (X = O, S, Br, Cl, and F) hydrogen bond in solution and solid states was previously reported for benzyl Meldrum's acid derivatives; see: Fillion, E.; Wilsily, A.; Fishlock, D. J. Org. Chem. 2009, 74, 1259-1267.
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(2009)
J. Org. Chem.
, vol.74
, pp. 1259-1267
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Fillion, E.1
Wilsily, A.2
Fishlock, D.3
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