New Odorless Protocols for the Synthesis of Aldehydes and Ketones from Thiol Esters

Synlett

Volumn , Issue 3, 2004, Pages 477-480

  Miyazaki, Tohru ^a   Han Ya, Yuki ^a   Tokuyama, Hidetoshi ^a   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Aldehyde; Ketone; Odorless dodecanethiol; Palladium catalyzed reaction; Thiol esters

Indexed keywords

ACETYLENE; ALDEHYDE; DODECANE; ESTER; KETONE; THIOESTER;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 1442286555     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815427     Document Type: Article

References (34)

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26. 1-Dodecanethiol is available from Aldrich at $22.90 (500 mL).
27. The enantiomeric excess of the dodecanethiol ester 4 was determined by HPLC (DAICEL Chiral-OD, 4.6 mm I.D. x 250 mm, 10% 2-propanol/n-hexane, 0.3 mL/min, 25°C).
28. 6b as a white crystalline solid (217 mg, 0.766 mmol, 71%).
29. The enantiomeric excess of dodecanethiol ester prepared from proline was determined by HPLC (DAICEL Chiral-OD, 4.6 mm I.D. x 250 mm, 10% 2-propanol/n-hexane, 0.5 mL/min, 25°C).
30. The enantiomeric excesses of the aldehydes prepared in entries 3 and 4 were determined by HPLC analysis after conversion of these aldehydes as described below (DAICEL Chiral-OD, 4.6 mm I.D. x 250 mm, 10% 2-propanol/n-hexane, 0.3 mL/min, 25°C, Scheme 3). matrix presented.
31. 7.6c (307 mg, 0.986 mmol, 94%) as a yellow oil.
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