Asymmetric Induction through Metalation of Chiral Dithioacetals and Oxathioacetals

The work presented in this article consists of synthesis of chiral dithioacetals and oxathioacetals using pure chiral auxiliaries, such as, (+) camphor, (−) menthol, and L-cysteine. Metalation of these chiral dithioacetals and oxathioacetals, followed by nucleophilic addition to benzaldehyde and rem...

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Bibliographic Details
Published inSynthetic communications Vol. 37; no. 17; pp. 2835 - 2845
Main Authors Zaidi, Javid H., Iqbal Gunjial, Naseem
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis Group 01.08.2007
Taylor & Francis
Subjects
Chemistry
Chemistry, Organic
dithioacetals
metalation
oxathioacetals
Physical Sciences
Science & Technology
dithioacetals
CARBANIONS
oxathioacetals
metalation
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Summary:The work presented in this article consists of synthesis of chiral dithioacetals and oxathioacetals using pure chiral auxiliaries, such as, (+) camphor, (−) menthol, and L-cysteine. Metalation of these chiral dithioacetals and oxathioacetals, followed by nucleophilic addition to benzaldehyde and removal of chiral auxiliary, furnished scalemic mandelic acid with various enantiomeric purities.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397910701471337