Please use this identifier to cite or link to this item:
https://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 | Citation: | 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 |
Appears in Collections: | Ph.D Theses (Open) |
Show full item record
Files in This Item:
File | Description | Size | Format | Access Settings | Version | |
---|---|---|---|---|---|---|
LEECHA.pdf | 1 MB | Adobe PDF | OPEN | None | View/Download |
Google ScholarTM
Check
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.