Conjugate addition of lithium enolates to aromatic carbonyl compounds complexed with aluminum tris(2,6-diphenylphenoxide) (ATPH)

Synlett

Volumn , Issue 1, 1999, Pages 81-83

  Saito, Susumu ^a   Sone, Toshihiko ^a   Shimada, Kazuto ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Aromatic; ATPH; Carbonyl; Conjugate addition; Ester enolate; LTMP

Indexed keywords

ALUMINUM DERIVATIVE; ALUMINUM TRIS(2,6 DIPHENYLPHENOXIDE); LITHIUM; UNCLASSIFIED DRUG;

ARTICLE; MOLECULAR INTERACTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032934223     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2527     Document Type: Article

References (20)

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5. (e) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. See also reference 5.
6. Nucleophilic addition to aromatic rings having the nitro group, see: (a) Makosza, M; Winiarski, J. Acc. Chem. Res. 1987, 20, 282.
7. Other dearomatization/functionalization sequences for rather inactivated aromatics, see: (b) Schultz, A. G.; Harrington, R. E.; Holoboski, M. A. J. Org. Chem. 1992, 57, 2973.
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11. (a) Maruoka, K.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 9091.
12. (b) Saito, S.; Shimada, K.; Yamamoto, H.; Martínez de Marigorta, E.; Fleming, I. Chem. Commun. 1997, 1299.
13. (c) Saito, S.; Shimada, K.; Ito, M.; Maruoka, K.; Yamamoto, H. in preparation.
14. 3Al (1 equiv) at rt under argon atmosphere, at which time methane gas evolved immediately (∼3.0 equiv). The resulting pale yellow solution was stirred at rt for 30 min, and used without further purification.
15. Stork, G.; Hudrlik, P. F. J. Am. Chem. Soc. 1968, 90, 4464.
16. As one of the referees suggested, the equilibrium of retro-addition - addition [complexed carbonyl compound + enolate = intermediate] becomes a serious problem depending on the aromatic substrate. For example, when the reaction mixture was stirred at 0 °C for 3h after addition of enolate la to a solution of the ATPH/benzaldehyde complex at -78 °C, not only 1,6-adduct 4a but also the 1,2-adduct were obtained in 49% and 29% yield, respectively. This means that the equilibrium still shifted to the right. In contrast, in a case where the intermediate, obtained by treatment of enolate 1a with the ATPH/ 1-indanone complex at -78 °C, was reacted under similar conditions (0 °C, 3h), the equilibrium significantly shifted to the left to give a quantitative recovery of 1-indanone. See entry 23 of Table 1, for comparison.
17. Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis, 1993, 1271.
18. 1H NMR analysis. (1S,2S)-(-)-trans-2-Phenyl-1 -cyclohexyl isobutyrate also gave disappointingly low de (6% de).
19. Bratovanov, S.; Bienz, S. Tetrahedron: Asymmetry 1997, 8, 1587.
20. 3: C, 69.21; H, 7.74. Found: C, 69.11; H, 7.91.