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Volumn 47, Issue 27, 2008, Pages 5026-5029

Highly diastereoselective, tandem, three-component synthesis of tetrahydrofurans from ketoaldehydes via silylated β-lactone intermediates

Author keywords

Cyclization; Mukaiyama aldol; Oxocarbenium ions; Synthetic methods; Tandem reactions

Indexed keywords

CHEMICAL REACTIONS; SILANES; SYNTHESIS (CHEMICAL);

EID: 49849095367     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800235     Document Type: Article
Times cited : (19)

References (53)
  • 1
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    • For reviews on tandem reactions, see: a, Eds, L. F. Tietze, H. P. Bell, G. Brasche, Wiley-VCH, Weinheim
    • For reviews on tandem reactions, see: a) Domino Reactions in Organic Synthesis (Eds.: L. F. Tietze, H. P. Bell, G. Brasche), Wiley-VCH, Weinheim, 2006;
    • (2006) Domino Reactions in Organic Synthesis
  • 17
    • 36649009510 scopus 로고    scopus 로고
    • for extension of this methodology to more highly substituted THFs using β-lactones by the TMAL process, see: T. A. Mitchell, D. Romo, J. Org. Chem. 2007, 72, 9053
    • b) for extension of this methodology to more highly substituted THFs using β-lactones by the TMAL process, see: T. A. Mitchell, D. Romo, J. Org. Chem. 2007, 72, 9053.
  • 18
    • 33845238277 scopus 로고    scopus 로고
    • For a recent review of THF synthesis, see
    • a) For a recent review of THF synthesis, see: J. P. Wolfe, M. B. Hay, Tetrahedron 2007, 63, 261;
    • (2007) Tetrahedron , vol.63 , pp. 261
    • Wolfe, J.P.1    Hay, M.B.2
  • 19
    • 40949128195 scopus 로고    scopus 로고
    • For selected recent examples, see
    • b) For selected recent examples, see: C. G. Nasveschuk, T. Rovis, J. Org. Chem. 2008, 73, 612;
    • (2008) J. Org. Chem , vol.73 , pp. 612
    • Nasveschuk, C.G.1    Rovis, T.2
  • 40
    • 53649091333 scopus 로고    scopus 로고
    • Ph.D. Thesis, Texas A & M University USA
    • C. Zhao, Ph.D. Thesis, Texas A & M University (USA), 2001.
    • (2001)
    • Zhao, C.1
  • 41
    • 53649097875 scopus 로고    scopus 로고
    • See the Supporting Information for stereochemical proof
    • See the Supporting Information for stereochemical proof.
  • 43
    • 53649090216 scopus 로고    scopus 로고
    • 1H NMR spectroscopic analysis supports the formation of a tetrahedral complex. See Ref. [15]. Mechanistic studies of the TMAL reaction will be described in a subsequent full paper.
    • 1H NMR spectroscopic analysis supports the formation of a tetrahedral complex. See Ref. [15]. Mechanistic studies of the TMAL reaction will be described in a subsequent full paper.
  • 44
    • 53649085799 scopus 로고    scopus 로고
    • Although tetrahedral zinc(II) complexes are the most common, several examples of trigonal-bipyramidal zinc(II) are known, see: a) R. H. Prince in Comprehensive Coordination Chemistry: Zinc and Cadmium, 5 Ed, G. Wilkinson, Pergamon, New York, 1987, pp. 925-1045;
    • Although tetrahedral zinc(II) complexes are the most common, several examples of trigonal-bipyramidal zinc(II) are known, see: a) R. H. Prince in Comprehensive Coordination Chemistry: Zinc and Cadmium, Vol. 5 (Ed.: G. Wilkinson), Pergamon, New York, 1987, pp. 925-1045;
  • 45
    • 0000447030 scopus 로고
    • Ed, S. J. Lippard, Wiley, New York
    • b) R. R. Holmes in Progress in Inorganic Chemistry, Vol. 32 (Ed.: S. J. Lippard), Wiley, New York, 1984, pp. 119-236;
    • (1984) Progress in Inorganic Chemistry , vol.32 , pp. 119-236
    • Holmes, R.R.1
  • 49
    • 37049124133 scopus 로고    scopus 로고
    • For examples of zinc(II) complexes containing a bidentate ligand that forms a four-membered ring with the metal center, see: a) M. Bonamico, G. Dessy, V. Fares, L. Scaramuzza, J. Chem. Soc. Dalton Trans. 1972, 2515;
    • For examples of zinc(II) complexes containing a bidentate ligand that forms a four-membered ring with the metal center, see: a) M. Bonamico, G. Dessy, V. Fares, L. Scaramuzza, J. Chem. Soc. Dalton Trans. 1972, 2515;


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.