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Volumn 66, Issue 26, 2010, Pages 4730-4737

Asymmetric syntheses of a GPR40 receptor agonist via diastereoselective and enantioselective conjugate alkynylation

Author keywords

Alkynyl acid; Cinchonidine; Conjugate addition; Diastereoselective; Enantioselective; GPR40; Oxazepanedione; Zincate

Indexed keywords

CINCHONIDINE; EPHEDRINE; G PROTEIN COUPLED RECEPTOR 40; G PROTEIN COUPLED RECEPTOR 40 AGONIST; HORMONE RECEPTOR STIMULATING AGENT; OXAZEPINE DERIVATIVE; UNCLASSIFIED DRUG; ZINC;

EID: 77955681257     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.019     Document Type: Article
Times cited : (28)

References (66)
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    • 77955699458 scopus 로고    scopus 로고
    • See Experimental Section.
    • See Experimental Section.
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    • For the review of the Meldrum's acids, see:
    • For the review of the Meldrum's acids, see:
  • 24
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    • B.C. Chen Heterocycles 32 1991 529 For recent examples of other conjugate additions using Meldrum's acids derived acceptors as the substrates, see:
    • (1991) Heterocycles , vol.32 , pp. 529
    • Chen, B.C.1
  • 35
    • 77955700553 scopus 로고    scopus 로고
    • For recent reviews of asymmetric conjugate alkynylation, see:
    • For recent reviews of asymmetric conjugate alkynylation, see:
  • 37
    • 66149109902 scopus 로고    scopus 로고
    • B.M. Trost, and A.H. Weiss Adv. Synth. Catal. 351 2009 963 For examples of enantioselective conjugate alkynylation of enones, see:
    • (2009) Adv. Synth. Catal. , vol.351 , pp. 963
    • Trost, B.M.1    Weiss, A.H.2
  • 44
    • 74949105179 scopus 로고    scopus 로고
    • O.V. Larionov, and E.J. Corey Org. Lett. 12 2010 300 For an example of rhodium-catalyzed enantioselective conjugate alkynylation of enals, see:
    • (2010) Org. Lett. , vol.12 , pp. 300
    • Larionov, O.V.1    Corey, E.J.2
  • 45
    • 70349988546 scopus 로고    scopus 로고
    • T. Nishimura, T. Sawano, and T. Hayashi Angew. Chem., Int. Ed. 48 2009 8057 For the example of rhodium-catalyzed asymmetric rearrangement of alkynyl alkenyl carbinols: synthetic equivalent to asymmetric conjugate alkynylation of enones, see:
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 8057
    • Nishimura, T.1    Sawano, T.2    Hayashi, T.3
  • 48
    • 77955681352 scopus 로고    scopus 로고
    • A variety of other chiral ligands and metals including copper, rhodium and lithium were also evaluated and gave lower yield and enantioselectivity.
    • A variety of other chiral ligands and metals including copper, rhodium and lithium were also evaluated and gave lower yield and enantioselectivity.
  • 49
    • 77955701019 scopus 로고    scopus 로고
    • 3N.
    • 3N.
  • 50
    • 77955683511 scopus 로고    scopus 로고
    • For similar zinc species see:
    • For similar zinc species see:
  • 57
    • 77955672933 scopus 로고    scopus 로고
    • Zincate is depicted as a monomer for clarity. Preliminary NMR studies indicate that several different zincate species exist in solution.
    • Zincate is depicted as a monomer for clarity. Preliminary NMR studies indicate that several different zincate species exist in solution.
  • 58
    • 77955707793 scopus 로고    scopus 로고
    • For full details, see Ref. 4.
    • For full details, see Ref. 4.
  • 59
    • 77955666538 scopus 로고    scopus 로고
    • Other solvents (Me-THF, MTBE, DME, toluene) evaluated provided lower ee (<80%) and yield (<90%);
    • Other solvents (Me-THF, MTBE, DME, toluene) evaluated provided lower ee (<80%) and yield (<90%);
  • 60
    • 77955695510 scopus 로고    scopus 로고
    • 2Zn were equally efficient;
    • 2Zn were equally efficient;
  • 61
    • 77955695509 scopus 로고    scopus 로고
    • Enantioselectivity was not dependent on the concentration (0.04-0.2 M);
    • Enantioselectivity was not dependent on the concentration (0.04-0.2 M);
  • 62
    • 77955702813 scopus 로고    scopus 로고
    • 2Zn/trifluoroethanol/cinchonidine) had no effect.
    • 2Zn/trifluoroethanol/cinchonidine) had no effect.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.