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Volumn 15, Issue 47, 2009, Pages 12926-12928

Allene carboxylates as dipolarophiles in Rh-catalyzed carbonyl ylide cycloadditions

Author keywords

Allenes; Axial chirality; Carbonyl ylides; Cycloaddition; Diazo compounds

Indexed keywords

[CARBONYL; ALLENES; AXIAL CHIRALITY; CARBONYL YLIDES; DIAZO COMPOUNDS;

EID: 73349133679     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902208     Document Type: Article
Times cited : (54)

References (41)
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    • Eds, N. Krause, A. S. K. Hashmi, VCH, Weinheim
    • a) Modern Allene Chemistry (Eds.: N. Krause, A. S. K. Hashmi), VCH, Weinheim, 2004;
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    • For reviews of chiral allenes, see: a
    • For reviews of chiral allenes, see: a) R. Rossi, P. Diversi, Synthesis 1973, 25-36;
    • (1973) Synthesis , pp. 25-36
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    • For recent examples, see: a
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    • Marshall, J.A.1    Chobanian, H.R.2
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    • Selected examples: a W. C. Agosta, J. Am. Chem. Soc. 1962, 84, 110-111;
    • Selected examples: a) W. C. Agosta, J. Am. Chem. Soc. 1962, 84, 110-111;
  • 20
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    • For reviews on the use of allenes in 1, 3-dipolar cycloaddiitons, see: a
    • For reviews on the use of allenes in 1, 3-dipolar cycloaddiitons, see: a) G. Broggini, G. Zecchi, Gazz. Chim. Ital. 1996, 126, 479-488;
    • (1996) Gazz. Chim. Ital , vol.126 , pp. 479-488
    • Broggini, G.1    Zecchi, G.2
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    • Eds, N. Krause, A. S. K. Hashmi, Wiley-VCH, Weinheim
    • M. Murakami, T. Matsuda in Modern Allene Chemistry (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim, 2004, pp. 727-815.
    • (2004) Modern Allene Chemistry , pp. 727-815
    • Murakami, M.1    Matsuda, T.2
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    • See the Supporting Information
    • See the Supporting Information.
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    • The increased temperatures required for these reactions, relative to related carbonyl ylide cycloadditions, may be due to the increased steric requirements of the allene relative to olefins and alkynes
    • The increased temperatures required for these reactions, relative to related carbonyl ylide cycloadditions, may be due to the increased steric requirements of the allene relative to olefins and alkynes.
  • 32
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    • Angew. Chem. Int. Ed. 2003, 42, 5351-5355;
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  • 34
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    • We are defining endo to be the product with the CO 2R3 group anti to the oxo bridge, as proposed by Padwa in reference [11a
    • 3 group anti to the oxo bridge, as proposed by Padwa in reference [11a].
  • 36
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    • While this analysis was only performed on the structures shown in Figure 2, all of the isolated products had very similar spectral characteristics within each diastereomeric series
    • While this analysis was only performed on the structures shown in Figure 2, all of the isolated products had very similar spectral characteristics within each diastereomeric series.
  • 38
    • 10844252156 scopus 로고    scopus 로고
    • T. M. V. D. Pinho e Melo, A. L. Cardoso, A. M. d'A. Rocha Gonsalves, J. Costa Pessoa, J. A. Paixão, A. M. Beja, Eur. J. Org. Chem. 2004, 4830-4839;
    • T. M. V. D. Pinho e Melo, A. L. Cardoso, A. M. d'A. Rocha Gonsalves, J. Costa Pessoa, J. A. Paixão, A. M. Beja, Eur. J. Org. Chem. 2004, 4830-4839;
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    • We attempted to use Marshall's Pd-catalyzed carbonylation of propargylic mesylates (Ref. [15a]) in order to construct enantioenriched 2e. Unfortunately, in our hands this method produced (S)-2e with moderate enantiopurity (72% ee). Because the diastereomeric relationship between 5 and 7 (and 6and 8) would complicate the determination of the enantiomeric excess in the product, we prefer to employ allenes with higher enantiopurity.
    • We attempted to use Marshall's Pd-catalyzed carbonylation of propargylic mesylates (Ref. [15a]) in order to construct enantioenriched 2e. Unfortunately, in our hands this method produced (S)-2e with moderate enantiopurity (72% ee). Because the diastereomeric relationship between 5 and 7 (and 6and 8) would complicate the determination of the enantiomeric excess in the product, we prefer to employ allenes with higher enantiopurity.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.