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|Title:||Part I: Organic reactions in non-conventional solvents Part II: New approach to the formation of bishomoallylic alcohols - synthesis of (R)-sulcatol||Authors:||CHEN SHUI LING||Keywords:||non-conventional solvents; asymmetric Mannich-type reaction; chiral auxiliary; Mukaiyama aldol reaction; bishomoallylic alcohols; kinetic resolution.||Issue Date:||17-Nov-2005||Citation:||CHEN SHUI LING (2005-11-17). Part I: Organic reactions in non-conventional solvents Part II: New approach to the formation of bishomoallylic alcohols - synthesis of (R)-sulcatol. ScholarBank@NUS Repository.||Abstract:||In Part I, we have successfully developed a number of useful, straightforward and interesting methodologies on the asymmetric Mannich-type reaction and the Mukaiyama aldol reaction using non-conventional solvents. Using L-valine methyl ester as a chiral amine in methanol or ionic liquids, the In(III)-complexes catalyzed asymmetric Mannich-type reaction proceeded smoothly with wide variety of aldehydes in high diastereoselectivities. A chiral auxiliary was designed and synthesis for the asymmetric Mannich-type reaction in water. In addition, we reported the first Mukaiyama aldol reaction using [omim]Cl in the absence of catalyst. We successfully increased the efficiency of this system by using a newly designed polar ionic liquid.The regioselectivity of nickel-catalyzed homoallylation was studied in Part II. At the mean time, we have successfully developed a chemical kinetic resolution of the bishomoallylic alcohols using In(OTf)3-catalyzed oxomiun ene-type cyclization with high enantioselectivities.||URI:||http://scholarbank.nus.edu.sg/handle/10635/14921|
|Appears in Collections:||Ph.D Theses (Open)|
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