This thesis documents the design and synthesis of chiral amino alcohol monomers 161, 162,167, chiral oxazolidine monomer 168 and chiral oxazolidinone monomers 203 and 204. The synthetic strategy relies on the key Suzuki coupling of aryl triflates derived from tyrosine with p-vinylphenylboronic acid where the resultant vinyl monomers are further modified to provide the desired functionality. / M...

The preparation of oxazolidinones by the hypervalent iodine mediated cyclization allylcarbamates is described. A versatile range substrates can be converted into substituted primed for further transformations. Derivatization products at both ends demonstrated. preliminary attempt enantioselective formation an oxazolidinone using a chiral iodane also presented.

The title compound, C(19)H(24)ClNO(5), was synthesized and subsequently employed in an Evans alkyl-ation. The purpose was to prove the absolute configuration in the projected synthesis of the side chain of (-)-Lytophilippine A. The oxazolidinone and the isopropylidene acetal rings have twisted conformations. The oxazolidinone and side-chain carbonyl groups are orientated in an anti-periplanar a...

The first organocatalyzed sulfoxidation reaction towards enantioenriched (R)-modafinil (Armodafinil®), a drug against narcolepsy, is reported here. A series of chiral organocatalysts, e.g., different chiral BINOL-phosphates, or a fructose-derived N-substituted oxazolidinone ketone (Shi catalyst) were applied for the sulfoxidation reaction with environmentally friendly H2O2 as a convenient oxyge...

The photooxygenation of oxazolidinone-substituted enecarbamates leads to diastereomerically pure dioxetanes. The high diastereoselectivity is rationalized in terms of effective pi-facial control achieved by shielding one side of the double bond with the chiral auxiliary. The absolute configuration of the dioxetanes is assigned by derivatization to diols.

an efficient, one-pot, four-component procedure for the synthesis of a small library of new chiral spiro- oxindolopyrrolidines with high regio-, diastereo- (>99:1 dr), and enantioselectivity (up to 80% ee) is described. in this process, the regio- and stereochemical 1,3-dipolar cycloaddition of azomethine ylides, which were generated insitu by the reaction of isatin derivatives and sarcosin,wit...

An efficient, one-pot, four-component procedure for the synthesis of a small library of new chiral spiro- oxindolopyrrolidines with high regio-, diastereo- (>99:1 dr), and enantioselectivity (up to 80% ee) is described. In this process, the regio- and stereochemical 1,3-dipolar cycloaddition of azomethine ylides, which were generated insitu by the reaction of isatin derivatives and sarcosin,wit...

A concise method is reported for the synthesis of 2-aminobicyclo[3.2.0]heptane-2,7-dicarboxylic acid, a close analogue glutamate receptor ligand LY354740, in both enantiomeric forms. The strategy features creation core structure at start via photochemical [2 + 2] cycloaddition reaction, an efficient resolution procedure using chiral oxazolidinone, and requires only minimal purification syntheti...

Asymmetric epoxidation of various styrenes using carbocyclic oxazolidinone-containing ketone 3 has been investigated. High enantioselectivity (89-93% enantiomeric excess) has been attained for this challenging class of alkenes. Mechanistic studies show that substituents on the ketone catalyst can have electronic influences on secondary orbital interactions, which affects the competition between...