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Volumn 13, Issue 10, 2011, Pages 2738-2741

Aminothiocarbamate-catalyzed asymmetric bromolactonization of 1,2-disubstituted olefinic acids

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BROMINATED HYDROCARBON; LACTONE;

EID: 79956160559     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200840e     Document Type: Article
Times cited : (130)

References (33)
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    • Examples of related halonium-induced cyclizations: Kang, S. H.; Lee, S. B.; Park, C. M. J. Am. Chem. Soc. 2003, 125, 15748-15749
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    • Early examples of asymmetric halolactonization reactions
    • Early examples of asymmetric halolactonization reactions: Haas, J.; Piguel, S.; Wirth, T. Org. Lett. 2002, 4, 297-300
    • (2002) Org. Lett. , vol.4 , pp. 297-300
    • Haas, J.1    Piguel, S.2    Wirth, T.3
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    • For a mechanistic discussion on the problems of enantioselective halocyclization, see
    • For a mechanistic discussion on the problems of enantioselective halocyclization, see: Brown, R. S. Acc. Chem. Res. 1997, 30, 131-137
    • (1997) Acc. Chem. Res. , vol.30 , pp. 131-137
    • Brown, R.S.1
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    • During the preparation of this paper, an elegant report appeared in the literature that is related to the asymmetric co-chlorination of 1,2-disubstituted olefins
    • During the preparation of this paper, an elegant report appeared in the literature that is related to the asymmetric co-chlorination of 1,2-disubstituted olefins: Jaganathan, A.; Garzan, A.; Whitehead, D. C.; Staples, R. J.; Borhan, B. Angew Chem., Int. Ed. 2011, 50, 2593-2596
    • (2011) Angew Chem., Int. Ed. , vol.50 , pp. 2593-2596
    • Jaganathan, A.1    Garzan, A.2    Whitehead, D.C.3    Staples, R.J.4    Borhan, B.5
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    • For details see the Supporting Information.
    • For details see the Supporting Information.
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    • 4), filtered, and concentrated in vacuo. The residue was purified by flash column chromatography to yield the corresponding product 7.
    • 4), filtered, and concentrated in vacuo. The residue was purified by flash column chromatography to yield the corresponding product 7.
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    • 2 was added as an additive.
    • 2 was added as an additive.
  • 28
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    • A small amount of 5-exolactone products was obtained when substrates 6n and 6o were used. For details, see the Supporting Information.
    • A small amount of 5-exolactone products was obtained when substrates 6n and 6o were used. For details, see the Supporting Information.
  • 32
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    • An extensive review on Lewis base catalysis
    • An extensive review on Lewis base catalysis: Denmark, S. E.; Beuter, G. L. Angew. Chem., Int. Ed. 2008, 47, 1560-1638
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    • No ee was observed when the alcohol substrate corresponding to acid 6a was used, which indicated that a substrate containing an acidic proton may be necessary.
    • No ee was observed when the alcohol substrate corresponding to acid 6a was used, which indicated that a substrate containing an acidic proton may be necessary.


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