- A mild, convenient synthesis of sulfinic acid salts and sulfonamides from alkyl and aryl halides
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A general, mild, and convenient method has been developed for the synthesis of various alkyl and aryl sulfinic acid salts and sulfonamides from the corresponding halides. Key to the success of this methodology is the design and facile synthesis of sodium 3-methoxy-3-oxopropane-1-sulfinate (SMOPS), a reagent that serves to introduce the protected sulfinate moiety directly to the substrate, thus avoiding the use of oxidizing and other harsh reaction conditions such as organolithium or Grignard reagents. Many functional groups, as well as heterocycles, are tolerated in the sequence.
- Baskin, Jeremy M,Wang, Zhaoyin
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p. 8479 - 8483
(2007/10/03)
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- Determination of absolute configuration of a metabolite (-)- hydroxyhexamide from acetohexamide, syntheses of (-)- and (+)- hydroxyhexamides and (-)- and (+)-acetoxyhexamides
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Enantioselective acetylation of (±)-4-(1- hydroxyethyl)benzenesulfonamide 6 with 'Acylase I' (No. A 2156) from Aspergillus melleus in the presence of vinyl acetate gave (R)-4-(1- acetoxyethyl)benzenesulfonamide 7 (98% ee) and (S)-6 (98% ee). Both (S)-6 and (R)-7 were individually converted to the (S)-hydroxyhexamide 2 (>99% ee) and (R)-hydroxyhexamide 2 (>99% ee), respectively. The absolute configuration of a metabolite (-)-hydroxyhexamide 2 from acetohexamide 1 was found to be S based on unequivocal chemical methods including X-ray analysis.
- Akita, Hiroyuki,Kurashima, Katsumi,Nozawa, Masako,Yamamura, Shigeo,Seri, Kenzi,Imamura, Yorishige
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p. 4331 - 4340
(2007/10/03)
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