Zemin Dong

Palladium (0) catalysed allylic sulfoximine to allylic sulfinamide rearrangement

Abstract Allylic sulfoximines (5) undergo a facile rearrangement to allylic sulfinamides (6) in the presence of a palladium (0) catalyst.

Palladium (0) catalysed rearrangements of allylic sulfoximines to allyl sulfinimidic acid esters and optically active N-Cbz protected γ-amino-enones

Abstract N -Tosyl allylic sulfoximines undergo rearrangement to allyl sulfinimidic acid esters in the presence of bidentate chiral ligands while N -Cbz allylic sulfoximines give optically active N -Cbz protected γ-amino-enones.

Diastereoselective synthesis of 1,4-amino alcohols via 1,4-stereochemical control using sulfoximines

Abstract A diastereoselective synthesis of 1,4-amino alcohols can be achieved from a highly diastereoselective reduction of a γ-keto-vinyl sulfoximine followed by C-methylation and then a highly diastereoselective palladium(0) catalysed allylic sulfoximine to allylic sulfinamide rearrangement with 1,4-stereochemical control from a remote hydroxyl group.

Chiral ligand-controlled diastereoselectivity and regioselectivity in palladium(0)-catalysed allylations

Abstract Diastereoselective allylations can be achieved on an epimeric mixture of optically active allylic benzoates having a fixed stereogenic centre allylic to the π-system using chiral ligands. The regiochemistry of these reactions is controlled by the chiral ligand and is different for the different diastereomeric complexes.

Diastereoselective reductions of β-substituted-γ-keto sulfoximines and a novel palladium(0)-catalysed allylic sulfoximine to allylic sulfinamide rearrangement

The reduction of β-substituted-γ-keto N-tosyl Sulfoximines is highly diastereoselective and the allylic sulfoximines products undergo a facile rearrangement to allylic sulfinamides in the presence of a palladium(0) catalyst.

Synthesis Of Chiral Allylic Amines Via Palladium(0) Catalysed Allylations Of Allylic Carbonates With Chiral Sulfinamide Anions

The palladium(0) catalysed allylation reactions of allylic carbonates with chiral sulfinamide anions to give unstable allylic sulfinamide products are described. These products are readily converted to stable, chiral N-benzoyl or N-tosyl allylic amine derivatives with poor to modest enantiomeric purities (ee 23-41%).

Diastereoselective Reactions and Rearrangements of Chiral Allylic Sulfoximines

Abstract: The nucleophilic and electrophilic chemistry of chiral allylic sulfominines and their alkyl sulfoximine counterparts are described including the synthesis of highly functionalised cyclopropanes derivatives. The synthesis of primary and secondary N-tosyl allylic amines via the palladium(0) catalysed rearrangement of allylic sulfoximines to allylic sulfinamides is also described.

Diasteoselective conjugate additions reactions of a lithiated allylic sulfoximine to acyclic enones

The conjugate addition reactions of lithiated N-p-tosyl S-phenyl-2-enyl sulfoximine 4 with cyclic and acyclic enones gives exclusively 1,4-α adducts, the reactions with acyclic enones are highly diastereoselective.

Diastereoselective Reactions of Allylic Sulfoximine Anions

Abstract The conjugate addition reactions of lithiated N-p-tolyl S-phenyl S-2-propenyl sulfoximine (4) with cyclic and acyclic enones gives exclusively 1,4-° adducts, the reactions with acyclic enones are highly diastereoselective.

Chiral sulfur compounds. Part 25. Diastereoselective 1,2-additions of lithiated (+)-(S)-N-tert-butyldiphenylsilyl-S-methyl-S-phenylsulfoximine to ketones

Lithiated (+)-(S)-N-tert-butyldiphenylsilyl-S-methyl-S-phenylsulfoximine 2f reacts with prochiral ketones to give a mixture of diastereoisomeric β-hydroxy sulfoximine adducts with a diastereoselection ranging from 79:21 to 98:2 depending upon the steric demand of the ketone. Racemic Chiral cyclic ketones react with 2f to give a mixture of diastereoisomeric β-hydroxy sulfoximine adducts which could be separated by a combination of column chromatography and recrystallization. Thermolysis of the diastereoisomerically pure adducts gave 2-alkylcyclohexanones in high enantiomeric purity. The relative stereochemistries of four of the β-hydroxy sulfoximine adducts have been unequivocally determined from single-crystal X-ray structural analysis. The stereochemical outcome of these 1,2-additions can best be rationalized by invoking competing boat transition states.