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Volumn 44, Issue 42, 2005, Pages 6924-6927

Deracemization of quaternary stereocenters by Pd-catalyzed enantioconvergent decarboxylative allylation of racemic β-ketoesters

Author keywords

Allylation; Asymmetric catalysis; Enolates; Palladium

Indexed keywords

CARBON; CHEMICAL BONDS; ESTERS; STEREOCHEMISTRY;

EID: 27544451620     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502018     Document Type: Article
Times cited : (329)

References (32)
  • 5
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    • Ref. [1]
    • For representative stereomutative examples, see: a) Ref. [1];
  • 6
    • 0000687774 scopus 로고    scopus 로고
    • (Eds: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York
    • b) A. Pfaltz, M. Lautens in Comprehensive Asymmetric Catalysis, Vol. 2 (Eds: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York, 1999, pp. 833-884;
    • (1999) Comprehensive Asymmetric Catalysis, Vol. 2 , vol.2 , pp. 833-884
    • Pfaltz, A.1    Lautens, M.2
  • 8
    • 27544509748 scopus 로고    scopus 로고
    • note
    • The term stereoablation describes the conversion of a chiral molecule to an achiral molecule (e.g., Figure 1, pathway II, (±)-A→C). Ablation from the Oxford English Dictionary meaning "the action or process of carrying away or removing; removal".
  • 11
    • 3042625080 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 2420-2423;
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 2420-2423
  • 14
    • 27544460434 scopus 로고    scopus 로고
    • note
    • To the best of our knowledge, there are no examples of the catalytic asymmetric synthesis of quaternary carbon stereocenters from racemates with quaternary stereocenters.
  • 15
    • 27544442015 scopus 로고    scopus 로고
    • A diastereoselective example of such a process has been recently reported, see: K. Xu, G. Lalic, S. M. Sheehan, M. D. Shair, Angew. Chem. 2005, 117, 2299-2301;
    • (2005) Angew. Chem. , vol.117 , pp. 2299-2301
    • Xu, K.1    Lalic, G.2    Sheehan, S.M.3    Shair, M.D.4
  • 16
    • 17644373114 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 2259-2261.
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 2259-2261
  • 21
    • 0000273585 scopus 로고    scopus 로고
    • and references therein
    • b) J. M. J. Williams, Synlett 1996, 705-710, and references therein.
    • (1996) Synlett , pp. 705-710
    • Williams, J.M.J.1
  • 22
    • 14844303302 scopus 로고    scopus 로고
    • Subsequent to our initial report, a similar transformation using a bisphosphine ligand was reported, see: B. M. Trost, J. Xu, J. Am. Chem. Soc. 2005, 127, 2846-2847.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 2846-2847
    • Trost, B.M.1    Xu, J.2
  • 23
    • 11844283363 scopus 로고    scopus 로고
    • An elegant alternative catalytic asymmetric alkylation of cyclic ketones for the synthesis of quaternary stereocenters has been recently described, see: A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2005, 127, 62-63.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 62-63
    • Doyle, A.G.1    Jacobsen, E.N.2
  • 24
    • 27544503368 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 27
    • 18744415432 scopus 로고    scopus 로고
    • For an excellent review on metal-catalyzed decarboxylation, see: J. A. Tunge, E. C. Burger, Eur. J. Org. Chem. 2005, 9, 1715-1726.
    • (2005) Eur. J. Org. Chem. , vol.9 , pp. 1715-1726
    • Tunge, J.A.1    Burger, E.C.2
  • 32
    • 27544497378 scopus 로고    scopus 로고
    • note
    • 3 was used as the ligand for the conversion of (±)-13 into (±)-14 and the meso isomer of 14 (not shown), a diastereomeric ratio of 70:30 was observed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.