Mimicking Dihydroxy Acetone Phosphate-Utilizing Aldolases through Organocatalysis: A Facile Route to Carbohydrates and Aminosugars†

Suri, Jeff T. ; Ramachary, Dhevalapally B. ; Barbas, Carlos F. (2005) Mimicking Dihydroxy Acetone Phosphate-Utilizing Aldolases through Organocatalysis: A Facile Route to Carbohydrates and Aminosugars† Organic Letters, 7 (7). pp. 1383-1385. ISSN 1523-7060

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Official URL: http://doi.org/10.1021/ol0502533

Related URL: http://dx.doi.org/10.1021/ol0502533

Abstract

A practical and environmentally friendly organocatalytic strategy designed to mimic the DHAP aldolases has been developed and shown to be effective in the preparation of carbohydrates and aminosugars. (S)-Proline and (S)-2-pyrrolidine-tetrazole catalyzed the aldol reaction between dihydroxy acetone variants such as 1,3-dioxan-5-one and 2,2-dimethyl-1,3-dioxan-5-one with aldehydes to give the corresponding polyols in good yields with very high ees.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:120801
Deposited On:05 Jul 2021 11:58
Last Modified:05 Jul 2021 11:58

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