Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/15073
Title: Development of new methodologies for the synthesis of enantiomerically enriched compounds
Authors: LEE CHENG HSIA, ANGELINE
Keywords: Homoallylic alcohols, Allyl transfer, Tandem reactions, olefin metathesis, Prins cyclization,
Issue Date: 28-Feb-2006
Source: LEE CHENG HSIA, ANGELINE (2006-02-28). Development of new methodologies for the synthesis of enantiomerically enriched compounds. ScholarBank@NUS Repository.
Abstract: The enantioselective syntheses of linear and cyclic homoallylic alcohols have been developed. These methodologies feature the following highlights: (1) epimerization was suppressed by using a milder acid and carrying out the reaction at lower temperatures; (2) first efficient method that controls, in situ, both the enantioselectivity and the olefinic geometry; (3) excess starting materials generated from the reaction can be recovered and reused; (4) olefin metathesis was achieved without protection of hydroxyl group in the presence of an acid. Subsequently, the preparation of stereo- and enantio-selective tetrahydropyrans by Prins cyclization was demonstrated. The significant features include: (1) preservation of stereochemical fidelity was achieved; (2) the utility of the allyl transfer and Prins cyclization methodologies in the enantioselective total synthesis of (-)-Centrolobine.
URI: http://scholarbank.nus.edu.sg/handle/10635/15073
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