Highly enantioselective construction of quaternary stereocenters on β-keto esters by phase-transfer catalytic asymmetric alkylation and Michael reaction

Angewandte Chemie - International Edition

Volumn 42, Issue 32, 2003, Pages 3796-3798

  Ooi, Takashi ^a   Miki, Takashi ^a   Taniguchi, Mika ^a   Shiraishi, Misato ^a   Takeuchi, Mifune ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Alkylation; Asymmetric synthesis; Michael addition; Phase transfer catalysis

Indexed keywords

CATALYSIS; KETONES; PHASE TRANSITIONS;

ASYMMETRIC SYNTHESIS;

ESTERS;

BETA KETO ESTER DERIVATIVE; ESTER; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; MICHAEL ADDITION; PHASE TRANSITION; STEREOCHEMISTRY;

EID: 0041363231     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351469     Document Type: Article

References (41)

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27. The results of the benzylation of 2 with other alkaline metal hydroxides under similar conditions are as follows: 2% yield, 45% ee with LiOH; 40% yield, 83% ee with NaOH.
28. 3-Ph); see entry 9 in Table 1 for comparison).
29. 1H NMR analysis of the corresponding (R) and (S) Mosher esters.[14]
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32. For recent reviews on catalytic asymmetric Michael reactions, see: a) N. Krause, A. Hoffman-Röder, Synthesis 2001, 171; b) M. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033; c) M. Kanai, M. Shibasaki in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley, New York, 2000, p. 569; d) K. Tomioka, Y. Nagaoka in Comprehensive Asymmetric Catalysis, Vol. 3 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, Chap. 31.1.
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36. For a recent successful example, see: a) Y Hamashima, D. Hotta, M. Sodeoka, J. Am. Chem. Soc. 2002, 124, 11240 and related references cited therein. This type of reaction by chiral phase-transfer catalysis has so far been unsuccessful; see: b) G. Szöllösi, M. Bartók, Chirality 2001, 13, 614.
37. With toluene as solvent, the enantioselectivity was slightly decreased (97% yield, 73% ee with 7a).
38. The absolute configuration of 9 was determined by comparison of the optical rotation with the reported value after conversion to the corresponding methyl ester.[10]
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41. For 3a, see: a) H. Falk, W. Fröstl, K. Schlögl, Tetrahedron Lett. 1974, 217; for the methylation product, see: b) K. Umemura, H. Matsuyama, M. Kobayashi, N. Kamigata, Bull. Chem. Soc. Jpn. 1989, 62, 3026.