Synthesis and reactivity of cyclic sulfamidites and sulfamidates

Ruthenium porphyrins [Ru(F20-TPP)(CO)] (F20-TPP = 5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato dianion) and [Ru(Por*)(CO)] (Por* = 5,10,15,20-tetrakis[(1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracen-9-yl]porphyrinato dianion) catalyzed intramolecular amidation of sulfamate esters p-X-C6H4(CH2)2OSO2NH2 (X = Cl, Me, MeO), XC6H4(CH2)3OSO2NH2 (X = p-F, p-MeO, m-MeO), and Ar(CH2)2OSO2NH2 (Ar = naphthalen-1-yl, naphthalen-2-yl) with PhI(OAc)2 to afford the corresponding cyclic sulfamidates in up to 89% yield with up to 100% substrate conversion; up to 88% ee was attained in the asymmetric intramolecular amidation catalyzed by [Ru(Por*)(CO)]. Reaction of [Ru(F20-TPP)(CO)] with PhINSO2OCH2CCl3 (prepared by treating the sulfamate ester Cl3CCH2OSO2NH2 with PhI(OAc)2) afforded a bis(imido)ruthenium(VI) porphyrin, [RuVI(F20-TPP)(NSO2OCH2CCl3)2], in 60% yield. A mechanism involving reactive imido ruthenium porphyrin intermediate was proposed for the ruthenium porphyrin-catalyzed intramolecular...

Intramolecular C-N bond formation reactions catalyzed by ruthenium porphyrins: amidation of sulfamate esters and aziridination of unsaturated sulfonamides.

Enantioselective synthesis of cyclic sulfamidates via Pd-catalyzed hydrogenation

Intramolecular PhIO Mediated Copper-Catalyzed Aziridination of Unsaturated Sulfamates: A New Direct Access to Polysubstituted Amines from Simple Homoallylic Alcohols

Sulfamic Acid and Its N- and O-Substituted Derivatives

Ring-opening of N-(PhF)serine-derived cyclic sulfamidate 17 was achieved with different nucleophiles (β-keto esters, β-keto ketones, dimethyl malonate, nitroethane, sodium azide, imidazole, and pot...

Scope and limitations in the use of N-(PhF)serine-derived cyclic sulfamidates for amino acid synthesis

Racemization in the use of N-(9-(9-phenylfluorenyl))serine-derived cyclic sulfamidates in the synthesis of delta-keto alpha-amino carboxylates and prolines.

Racemization in the Use of N‐(9‐(9‐Phenylfluorenyl))serine‐derived Cyclic Sulfamidates in the Synthesis of δ‐Keto α‐Amino Carboxylates and Prolines.

N-(9-(9-Phenylfluorenyl))homoserine-Derived Cyclic Sulfamidates: Novel Chiral Educts for the Synthesis of Enantiopure γ-Substituted α-Amino Acids.

Scope and Limitations in the Use of N‐(PhF)Serine‐Derived Cyclic Sulfamidates for Amino Acid Synthesis.

Lan Wei

Papers

Scope and limitations in the use of N-(PhF)serine-derived cyclic sulfamidates for amino acid synthesis

Racemization in the use of N-(9-(9-phenylfluorenyl))serine-derived cyclic sulfamidates in the synthesis of delta-keto alpha-amino carboxylates and prolines.

Racemization in the Use of N‐(9‐(9‐Phenylfluorenyl))serine‐derived Cyclic Sulfamidates in the Synthesis of δ‐Keto α‐Amino Carboxylates and Prolines.

N-(9-(9-Phenylfluorenyl))homoserine-Derived Cyclic Sulfamidates: Novel Chiral Educts for the Synthesis of Enantiopure γ-Substituted α-Amino Acids.

Scope and Limitations in the Use of N‐(PhF)Serine‐Derived Cyclic Sulfamidates for Amino Acid Synthesis.