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Volumn 49, Issue 3, 2010, Pages 568-571

Catalytic enantio- and diastereoselective alkylations with cyclic sulfamidates

Author keywords

Alkylation; Contiguous stereocenters; Phase transfer catalysis; Ring opening reactions; Sulfur heterocycles

Indexed keywords

ASYMMETRIC PHASE; DIASTEREOSELECTIVE; DIASTEREOSELECTIVE ALKYLATION; ENANTIO; ENANTIOSELECTIVITES; GOOD YIELD; NUCLEOPHILIC RING OPENING; PHASE TRANSFER CATALYSIS; RING OPENING REACTION; STEREOCENTERS; SULFUR HETEROCYCLES;

EID: 74549149104     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200905329     Document Type: Article
Times cited : (37)

References (46)
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    • For examples of azetidinium ions used as electrophiles with carbon nucleophiles, see
    • For examples of azetidinium ions used as electrophiles with carbon nucleophiles, see: F. Couty, O. David, B. Drouillat, Tetrahedron Lett. 2007, 48, 9180.
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  • 8
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    • For a comprehensive review on the synthesis and reactions of cyclic sulfamidates, see
    • For a comprehensive review on the synthesis and reactions of cyclic sulfamidates, see: R. E. Melendez, W. D. Lubell, Tetrahedron 2003, 59, 2581.
    • (2003) Tetrahedron , vol.59 , pp. 2581
    • Melendez, R.E.1    Lubell, W.D.2
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    • For selected reports of phase-transfer-catalyzed alkylations forming a quaternary stereocenter, see: a
    • For selected reports of phase-transfer-catalyzed alkylations forming a quaternary stereocenter, see: a) U. H. Dolling, P. Davis, E.J.J. Grabowski, J. Am. Chem. Soc. 1984, 106, 466;
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 466
    • Dolling, U.H.1    Davis, P.2    Grabowski, E.J.J.3
  • 41
    • 74549141804 scopus 로고    scopus 로고
    • CCDC 753701 (3d) and 753702 (5c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via
    • CCDC 753701 (3d) and 753702 (5c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data- request/cif.
  • 42
    • 74549174131 scopus 로고    scopus 로고
    • Subjection of acyclic pro-nucleophile tert-butyl-2-methylacetoacetate to our optimal conditions resulted in a 2:3 inseparable mixture of O- and C-alkylated products, respectively.
    • Subjection of acyclic pro-nucleophile tert-butyl-2-methylacetoacetate to our optimal conditions resulted in a 2:3 inseparable mixture of O- and C-alkylated products, respectively.
  • 43
    • 74549140934 scopus 로고    scopus 로고
    • The stereochemistry of indanone adducts 3 b, 3 c, 3e-3h were assigned by analogy to compound 3d (absolute configuration determined by X-ray crystallography). Compounds 3j and 31 were assigned by analogy to the cyclopentanone system (see Ref. [13c]). Succinimide products 3i and 3m were assigned by analogy to compound 5 c in the matched system with (S)-1f and catalyst 4a (relative configuration determined by X-ray crystallography). Glutarimide adducts 3a and 3k were assigned by analogy to the succinimide, and cyclohexanone systems (Ref. [13]).
    • The stereochemistry of indanone adducts 3 b, 3 c, 3e-3h were assigned by analogy to compound 3d (absolute configuration determined by X-ray crystallography). Compounds 3j and 31 were assigned by analogy to the cyclopentanone system (see Ref. [13c]). Succinimide products 3i and 3m were assigned by analogy to compound 5 c in the matched system with (S)-1f and catalyst 4a (relative configuration determined by X-ray crystallography). Glutarimide adducts 3a and 3k were assigned by analogy to the succinimide, and cyclohexanone systems (Ref. [13]).
  • 44
    • 74549132544 scopus 로고    scopus 로고
    • Acyclic ethyl phenylcyanoacetate gave product 5e with (S)-1f and 4a (10 mol%) in an 84% yield and 3:2 d.r. (see the Supporting Information).
    • Acyclic ethyl phenylcyanoacetate gave product 5e with (S)-1f and 4a (10 mol%) in an 84% yield and 3:2 d.r. (see the Supporting Information).
  • 45
    • 35549006377 scopus 로고    scopus 로고
    • An electrophile-directed diastereoselective alkylation has recently been described
    • An electrophile-directed diastereoselective alkylation has recently been described: S. P. Marsden, R. Newton, J. Am. Chem. Soc. 2007, 129, 12600.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 12600
    • Marsden, S.P.1    Newton, R.2
  • 46
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    • When the reaction was conducted with racemic 1g, a 1:1 mixture of diastereomers was obtained (see the Supporting Information)
    • When the reaction was conducted with racemic 1g, a 1:1 mixture of diastereomers was obtained (see the Supporting Information).


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