ORGN 455 |
| Xu Bai, Yinghuan Fu, Jinchang Wu, and Tonghao Wu. Center for Combinatorial Chemistry and Drug Discovery, Jilin University, 75 Jinlai St., Changchun, Jilin 130012, China |
| In the effort to synthesize polymer-immobilized chiral amino alcohol, we investigated the preparation of compound 1 and its application in asymmetric synthesis in solution phase as a model study of solid phase reaction. Thus, compound 1 was synthesized in high yield from commercially available starting material D-(-)-4-hydroxyphenylglycine by sequential reactions of protection, esterification, reduction and finally etherification with benzyl chloride (mimics of Merrifield resin) under basic condition. Subsequently, compound 1 was condensed with 1-naphthaldehyde 2 to provide oxazolidine 3, which was utilized as a versatile intermediate for the formation of a variety of chiral products in good yield with high enantiomeric excess as in the scheme. This study demonstrated the feasibility of Merrifield resin-immobilized chiral amino alcohol in asymmetric synthesis. |
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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Division of Organic Chemistry |
