Development of new asymmetric two-center catalysts in phase-transfer reactions

Tetrahedron Letters

Volumn 43, Issue 52, 2002, Pages 9539-9543

  Shibuguchi, Tomoyuki ^a   Fukuta, Yuhei ^a   Akachi, Yoko ^a   Sekine, Akihiro ^a   Ohshima, Takashi ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Alkylation; Asymmetric two center catalyst; Michael addition; Phase transfer catalysis

Indexed keywords

ACRYLIC ACID DERIVATIVE; AMMONIA; GLYCINE DERIVATIVE; SCHIFF BASE; TARTARIC ACID;

ALKYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; ENANTIOSELECTIVITY; MICHAEL ADDITION; MONTE CARLO METHOD; PHASE TRANSITION; SCREENING;

EID: 0037164678     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02416-4     Document Type: Article

References (41)

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30. 2 (Accelrys Inc., San Diego, CA and Cambridge, UK). The conformation depicted in Fig. 1 was obtained using a random conformational search, the so-called Monte Carlo method, followed by a molecular mechanics minimization calculation (Universal Force Field v.1.02, see: Rappe, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A.; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024).
31. For example, (Sigma-Aldrich Co., St. Louis, MO), L-tartaric acid: 100 g, 4100 yen (ca. 33 US$), diethyl L-tartrate: 100 g, 8600 yen (ca. 70 US$), quinine: 100 g, 78000 yen (ca. 640 US$) and (R)-BINOL: 100 g, 783000 yen (ca. 6420 US$).
32. In preliminary studies, N, N, N′N′-tetraalkyl-N, N′-dibenzyl type bis-ammonium salts were not effective catalysts in terms of enantioselectivity.
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37. 2=7:3) enhanced reactivity efficiently without any loss of selectivity. In the case of phase-transfer Michael additions, halobenzenes showed better selectivity than do other aromatic solvents, such as benzene and toluene. Although 1,2,4-trichlorobenzene gave the best selectivity, we eventually selected chlorobenzene based on reactivity.
38. Degassed conditions did not improve the results. Thus, the reaction atmosphere was simply replaced with flowing argon.
39. Absolute configurations of the products shown in Tables 1-4 were determined based on the previous reports, see: Ishikawa, T.; Araki, Y.; Kumamoto, T.; Seki, H.; Fukuda, K.; Isobe, T. Chem. Commun. 2001, 245. See also Ref. 3a.
40. Because of the relatively high melting point of chlorobenzene (-45°C), -30°C should be the lowest temperature used in this system. Other solvents, such as toluene, had worse selectivity.
41. Recently, spiro-type phase-transfer catalyst derived from L-tartrate was synthesized by Arai, S., Tsuji, R. and Nishida, A. (private communication).