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Volumn , Issue 1, 2004, Pages 128-134

[3,3]-Sigmatropic Rearrangements in the Enantioselective Synthesis of (-)-Methylenolactocin

Author keywords

Asymmetric synthesis; Dihidroxylations; Diols; Rearrangement

Indexed keywords

CATALYST ACTIVITY; ESTERS; KETONES; PALLADIUM;

EID: 0346057822     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-44351     Document Type: Article
Times cited : (28)

References (61)
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    • (11) In this connection it should be pointed out that the reduction of related alk-2-ene-1,4-diones gives lower stereoselectivities: (a) Bach, J.; Berenguer, R.; Garcia, J.; López, M.; Manzanal, J.; Vilarrasa, J. Tetrahedron 1998, 54, 14947. (b) Bach, J.; Berenguer, R.; Garcia, J.; Loscertales, T.; Manzanal, J.; Vilarrasa, J. Tetrahedron Lett. 1997, 38, 1091.
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    • In this connection it should be pointed out that the reduction of related alk-2-ene-1,4-diones gives lower stereoselectivities: (a) Bach, J.; Berenguer, R.; Garcia, J.; López, M.; Manzanal, J.; Vilarrasa, J. Tetrahedron 1998, 54, 14947. (b) Bach, J.; Berenguer, R.; Garcia, J.; Loscertales, T.; Manzanal, J.; Vilarrasa, J. Tetrahedron Lett. 1997, 38, 1091.
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    • An attempt to obtain (S,S)-5 by double addition of acetylene to hexanal under similar conditions also failed, see: Sasaki, H.; Boyall, D.; Carreira, E. M. Helv. Chim. Acta 2001, 84, 964.
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    • note
    • 19F NMR and HPLC), we assumed that its optical purity should be ≥98% ee on the basis of that found for (S,S)-3. Absolute configuration of diol 3 revealed it to be identical to that obtained from reduction of diketone 5.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.