Dilithium 2,2'-methylenebis(4,6-di-tert-butylphenoxide) as a bidentate Lewis acid in organic synthesis

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3745-3748

  Ooi, Takashi ^a   Saito, Akira ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACROLEIN; CARBONYL DERIVATIVE; COORDINATION COMPOUND; CYCLOPENTADIENE DERIVATIVE; LITHIUM DERIVATIVE; OXIDE; REAGENT;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

BETULACEAE;

EID: 0032575140     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00575-9     Document Type: Article

References (15)

1. (1) Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595.
2. (2) Grieco, P. A. Aldrichimica Acta 1991, 24, 59 and references cited therein.
3. (3) Chini, M.; Crotti, P.; Favero, L.; Macchia, F. Tetrahedron Lett. 1994, 35, 761.
4. (4) Handy, S. T.; Grieco, P. A.; Mineur, C.; Ghosez, L. Synlett 1995, 565.
5. (5) Barbarich, T. J.; Handy, S. T.; Miller, S. M.; Anderson, O.P.; Grieco, P. A.; Strauss, S. H. Organometallics 1996, 15, 3776.
6. (6) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707.
7. (7) (a) Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307.
8. (b) Ooi, T.; Tayama, E.; Takahashi, M.; Maruoka, K. Tetrahedron Lett. 1997, 38, 7403.
9. (8) 2,7-Dimethyl-1,8-biphenylenediol is already found to be an appropriate spacer for designing bidentate aluminum reagent (see ref 7). However, dilithium reagent derived from 2,7-dimethyl-1,8-biphenylenediol and BuLi is sparingly soluble in toluene and even in diethyl ether.
10. (9) For the preparation of 2,2′-dihydroxydiphenylmethanes: (a) Casiraghi, G.; Casnati, G.; Pochini, A.; Puglia, G.; Ungaro, R.; Sartori, G. Synthesis 1981, 143.
11. (b) Casiraghi, G.; Casnati, G.; Cornia, M.; Pochini, A.; Puglia, G.; Sartori, G.; Ungaro, R. J. Chem. Soc. Perkin I 1974, 318.
12. 3Al exhibits almost the same reactivity with that of (2,7-dimethyl-1,8-biphenylenedioxy)bis(dimethylaluminum).
13. 2 = Me) in 16.6% yield.
14. (12) Attempted cycloaddition of methyl acrylate and cyclopentadiene with 1 proceeds quite reluctantly at room temperature.
15. 4/diethyl ether system proceeds faster at room temperature and it is apparently possible to obtain synthetically useful chemical yield employing more concentrated conditions.