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Volumn 46, Issue 28, 2007, Pages 5325-5328

Catalytic asymmetric formation of δ-lactones by [4+2] cycloaddition of zwitterionic dienolates generated from α,β-unsaturated acid chlorides

Author keywords

lactones; Cinchona alkaloids; Cycloaddition; Hetero Diels Alder reaction; Organocatalysis

Indexed keywords

CINCHONA ALKALOIDS; ORGANOCATALYSIS; UNSATURATED ACID CHLORIDES;

EID: 34447574865     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200700859     Document Type: Article
Times cited : (82)

References (63)
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    • selected leading references: c) G. R. Weihe, T. C. McMorris, J. Org. Chem. 1978, 43, 3942;
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    • General review on HDA reactions: K. A. Jørgensen, Angew. Chem. 2000, 112, 3702;
    • General review on HDA reactions: K. A. Jørgensen, Angew. Chem. 2000, 112, 3702;
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  • 27
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    • A single example using an α,β-unsaturated aldehyde was reported, see
    • A single example using an α,β-unsaturated aldehyde was reported, see Ref. [12].
    • , vol.12
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    • 2-(Trimethylsilyl)vinylketene has been reported to be a remarkable stable vinylketene and has been used for non-enantioselective HDA reactions
    • 2-(Trimethylsilyl)vinylketene has been reported to be a remarkable stable vinylketene and has been used for non-enantioselective HDA reactions: D. M. Bennett, I. Okamoto, R. L. Danheiser, Org. Lett. 1999, 1, 641.
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    • Bennett, D.M.1    Okamoto, I.2    Danheiser, R.L.3
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    • f) review on the use of ketenes in asymmetric synthesis: R. K. Orr, M. A. Calter, Tetrahedron 2003, 59, 3545;
    • (2003) Tetrahedron , vol.59 , pp. 3545
    • Orr, R.K.1    Calter, M.A.2
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    • reviews on the history of ketene chemistry: g) T. T. Tidwell, Eur. J. Org. Chem. 2006, 563;
    • (2006) Eur. J. Org. Chem , pp. 563
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    • selected leading references: b D. A. Jackson, M. Rey, A. S. Dreiding, Tetrahedron Lett. 1983, 24, 4817;
    • selected leading references: b) D. A. Jackson, M. Rey, A. S. Dreiding, Tetrahedron Lett. 1983, 24, 4817;
  • 43
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    • 2NHEt]Cl is formed.
    • 2NHEt]Cl is formed.
  • 44
    • 13644264785 scopus 로고    scopus 로고
    • Yield of 6a: 55-76, decreasing values in this order: M, Er III, SnII, ScIII, NdIII, In III, CuII, YbIII, LiI, Sm III, ZrIV, AlIII, MgII, Gd III, BiIII, EuIII, ZnII, Y III. The combination of cinchona alkaloid derivatives and metal triflate salts was previously successfully applied to [2+2] cycloadditions of ketenes. See: S. France, M. H. Shah, A. Weatherwax, H. Wack, J. P. Roth, T. Lectka, J. Am. Chem. Soc. 2005, 127, 1206 and Ref, 18e
    • III. The combination of cinchona alkaloid derivatives and metal triflate salts was previously successfully applied to [2+2] cycloadditions of ketenes. See: S. France, M. H. Shah, A. Weatherwax, H. Wack, J. P. Roth, T. Lectka, J. Am. Chem. Soc. 2005, 127, 1206 and Ref. [18e].
  • 45
    • 34447538835 scopus 로고    scopus 로고
    • The absolute configuration of δ-lactone 6f was determined by chemical correlation. For details see the Supporting Information.
    • The absolute configuration of δ-lactone 6f was determined by chemical correlation. For details see the Supporting Information.
  • 47
    • 34447518088 scopus 로고    scopus 로고
    • Theoretical studies of HAD reactions have revealed that the mechanism can change from a concerted nonsynchronous to a stepwise mechanism depending on the substituents on the reacting species and on the reaction conditions. See for example: a L. F. Tietze, J. Fennen, E. Anders, Angew. Chem. 1989, 101, 1420;
    • Theoretical studies of HAD reactions have revealed that the mechanism can change from a concerted nonsynchronous to a stepwise mechanism depending on the substituents on the reacting species and on the reaction conditions. See for example: a) L. F. Tietze, J. Fennen, E. Anders, Angew. Chem. 1989, 101, 1420;
  • 53
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    • Based on literature precedent for the hydrolysis of β- trichloromethyl-β-lactones (H. Wynberg, E. G. J. Staring, J. Chem. Soc. Chem. Commun. 1984, 1181)
    • Based on literature precedent for the hydrolysis of β- trichloromethyl-β-lactones (H. Wynberg, E. G. J. Staring, J. Chem. Soc. Chem. Commun. 1984, 1181)
  • 54
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    • N2 ring opening. Oxidation of primary alcohol 10 providing 7 revealed the same configuration for 10 (see the Supporting Information).
    • N2 ring opening. Oxidation of primary alcohol 10 providing 7 revealed the same configuration for 10 (see the Supporting Information).
  • 59
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    • See Ref. [23] and a M. E. Jung, G. Piizzi, J. Org. Chem. 2002, 67, 3911;
    • See Ref. [23] and a) M. E. Jung, G. Piizzi, J. Org. Chem. 2002, 67, 3911;
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    • The relative configuration of 13 was assigned by NOE experiments: see the Supporting Information for details.
    • The relative configuration of 13 was assigned by NOE experiments: see the Supporting Information for details.
  • 63
    • 34447519704 scopus 로고    scopus 로고
    • Product 11 is a mixture of three compounds with different groups X, which can be F, OH, or an O bridge in a dimeric species.
    • Product 11 is a mixture of three compounds with different groups X, which can be F, OH, or an O bridge in a dimeric species.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.