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Volumn 38, Issue 12, 1999, Pages 1803-1805

Regio- and stereoselective synthesis of γ-alkylidenebutenolides by cyclization of dilithiated 1,3-dicarbonyl compounds with N,N′-dimethoxy-N,N′-dimethylethanediamide

Author keywords

Butenolides; C C coupling; Dianions; Lactones; Stereoselective syntheses

Indexed keywords

BUTENOLIDE; CARBONYL DERIVATIVE; DIAMIDE; LACTONE DERIVATIVE; LITHIUM DERIVATIVE; N,N' DIMETHOXY N,N' DIMETHYLETHANEDIAMIDE; NATURAL PRODUCT; OXALIC ACID; UNCLASSIFIED DRUG;

EID: 0033553820     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990614)38:12<1803::AID-ANIE1803>3.0.CO;2-5     Document Type: Article
Times cited : (71)

References (43)
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    • e) there is one report in which good stereoselectivities were observed for the preparation of α,β-dimethoxy-γ-alkylidenebutenolides by β-elimination: M. A. Khan, H. Adams, Synthesis 1995, 687-692.
    • (1995) Synthesis , pp. 687-692
    • Khan, M.A.1    Adams, H.2
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    • ref. [1]
    • c) ref. [1].
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    • a) For the preparation of dianions from 1,3-dicarbonyl compounds, see L. Weiler, J. Am. Chem. Soc. 1970, 92, 6702-6704;
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 6702-6704
    • Weiler, L.1
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    • (Houben-Weyl), 4th ed.
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    • (1993) Methoden Org. Chem. , vol.E19D , pp. 448-566
    • Maercker, A.1
  • 30
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    • Cyclizations of dianions with dielectrophiles are significantly less common than condensation reactions with monofunctional electrophiles: a) K. G. Bilyard, P. J. Garratt, R. Hunter, E. Lete, J. Org. Chem. 1982, 47, 4731-4736;
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    • Bilyard, K.G.1    Garratt, P.J.2    Hunter, R.3    Lete, E.4
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    • Review of the structure and reactivity of lithium enolates: D. Seebach, Angew. Chem. 1988, 100, 1685-1715;
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    • Seebach, D.1
  • 43
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    • For decarbonylation reactions that occur during the cyclization of glycols with oxalyl chloride, see T. Iida, T. Itaya, Tetrahedron 1993, 49, 10511-10530.
    • (1993) Tetrahedron , vol.49 , pp. 10511-10530
    • Iida, T.1    Itaya, T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.