Journal
JOURNAL OF HETEROCYCLIC CHEMISTRY
Volume 58, Issue 9, Pages 1878-1882Publisher
WILEY
DOI: 10.1002/jhet.4286
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Funding
- Council of Scientific and Industrial Research, New Delhi, India
- University Grand Commission (UGC)
- DST-FIST
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This method utilizes Sc(OTf)(3) as a catalyst and (-)-menthol as a chiral auxiliary to achieve remarkable diastereoselectivity in the asymmetric aldol reaction. It offers mild reaction conditions, high yields, and excellent diastereoselectivity with a variety of substituted aromatic aldehydes. Sc(OTf)(3) demonstrates excellent diastereoselectivity at -45 degrees C under different reaction conditions.
This method involves the direct asymmetric aldol reaction of (-)-menthyl isothiocyanatoacetate 5 with a variety of substituted aromatic aldehydes, which offers a convenient method for the synthesis of intermediate containing biologically relevant alpha-amino beta-hydroxyl groups in oxazolidine ring. In this methodology, the products show remarkable diastereoselectivity using Sc(OTf)(3) as a catalyst and easily accessible (-)-menthol as a chiral auxiliary. This approach includes some important aspects such as mild reaction conditions, high yields, and excellent diastereoselectivity with a number of substituted aromatic aldehydes. The optimization and effect of different catalysts were studied at different reaction conditions and it is found that Sc(OTf)(3) shows excellent diastereoselectivity at -45 degrees C.
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