329770-66-3

Upstream product

• 33993-53-2 N,S-dimethyl-S-phenylsulfoximine 
• 5664-21-1 cyclohexylacetaldehyde 
• 329770-65-2 (+)-(E,S)-N-methyl-S-(3-cyclohexyl-1-propenyl)-S-phenylsulfoximine 

Downstream Products

• 329770-98-1 (+)-(E)-(1R,2R)-4-cyclohexyl-2-[(S)-N-methyl-S-phenylsulfonimidoyl]-1-phenylbut-3-en-1-ol 
• 445010-35-5 C₆H₁₁C₁₈H₂₇O₅N₂S₂ 
• 445010-40-2 C₆H₅C₁₈H₂₇O₅N₂S₂ 
• 616234-12-9 (+)-(E,S_S,2S,3R)-5-[N-methyl-S-phenylsulfonimidoyl]-3-cyclohexyl-2-[(2-methylprop-2-yl-sulfonyl)-prop-2-ynyl-amino]pent-4-enoic acid ethyl ester 

Relevant academic research and scientific papers

Asymmetric aziridination with chiral allyl aminosulfoxonium ylides: synthesis of alkenyl aziridine carboxylates and palladium-catalyzed E,trans/E,cis-isomerization of an alkenyl aziridine

Chiral cyclic and acyclic allyl aminosulfoxonium ylides have been generated from aminosulfoxonium-substituted β,γ-unsaturated α-amino acids (method A) and 1-alkenyl aminosulfoxonium salts (method B) upon treatment with DBU. Their application to the asymme

Functionalized chiral vinyl aminosulfoxonium salts: Asymmetric synthesis and application to the synthesis of enantiopure unsaturated prolines, β,γ-dehydro amino acids, and cyclopentanoid keto aminosulfoxonium ylides

Methylation of the enantiopure functionalized vinyl sulfoximines 5a-e and 14a-d followed by a F- ion or DBU-mediated isomerization of the vinyl aminosulfoxonium salts 7a-e and 15a-d, respectively, gave the allyl aminosulfoxonium salts 10a-e and 17a-d, res

N-methylsulfonimidoyl-substituted (2-alkenyl)titanium complexes: Application to the synthesis of β- and δ-sulfonimidoyl-substituted chiral homoallylic alcohols, x-ray crystal structure analysis, and fluxional behavior

Enantiopure acyclic (E)- and (Z)-configured allylic sulfoximines have been synthesized from N,S-dimethyl-S-phenylsul-foximine and aldehydes by the addition-elimination-isomerization route through the intermediate generation of the corresponding (E)-configured vinylic sulfoximines. Isomerization of the vinylic sulfoximines with DBU preferentially afforded the corresponding (Z)-configured allylic sulfoximines, which were subsequently isomerized by DBU to preferentially yield the (E)-isomers. Titanation of lithiated (E)-configured allylic sulfoximines with ClTi(OiPr)3 furnished the corresponding bis(2-alkenyl)diisopropyloxytitanium(IV) complexes, which reacted with aldehydes in the presence of ClTi(OiPr)3 with high regio- and diastereoselectivities at the γ-position to give the corresponding (Z)-anti-configured δ-N-methylsulfonimidoyl-substituted homoallylic alcohols in good yields. In the absence of ClTi(OiPr)3 at low temperatures, only one allylic moiety of the bis(alkenyl) diisopropyloxytitanium complex is transferred to the aldehyde. In this way, a cyclic lithiated allylic sulfoximine has been converted with high regio- and diastereoselectivity to the corresponding homoallylic alcohols bearing a vinylic sulfonimidoyl group. Titanation of lithiated (E)- and (Z)-configured allylic sulfoximines with ClTi(NEt2)3 afforded the corresponding mono(2-alkenyl)tris (diethylamino)titanium(IV) complexes, which reacted with aldehydes with moderate to high regioselectivities and high diastereoselectivities preferentially at the α-position to give the corresponding syn-configured β-N-methylsulfonimidoyl-substituted homoallylic alcohols along with the (Z)-anti-configured δ-N-methylsulfonimidoyl-substituted homoallylic alcohols in good yields. In this way, the cyclic lithiated allylic sulfoximine was converted with high regio- and diastereoselectivity to the corresponding isomeric homoallylic alcohols bearing an allylic sulfonimidoyl group. In the case of mono(alkenyl)tris(diethylamino)titanium(IV) complexes, the regioselectivity of their reactions with aldehydes has been found to depend on the size of the substituent at the CC double bond and the aldehyde, as well as on the configuration of the double bond. Reaction of racemic lithiated N-methyl-S-(3,3-diphenyl-2-propenyl)-S-phenylsul-foximine with ClTi(OiPr)3 afforded the corresponding bis(alkenyl) diisopropyloxytitanium(IV) complex. X-ray structure analysis revealed a distorted octahedral cis,cis,cis-configured bis(2-alkenyl)diisopropyloxytitanium(IV) complex, in which the allylic moieties are coordinated in a bidentate fashion through C-α and the N atom to the Ti atom, both having the relative configuration RsSc. In solution, the titanium complex shows fluxional behavior, which is Characterized by topomerization of the isopropyloxy groups and allylic moieties. The exchange of the latter occurs with retention of the configuration at C-α.