286454-85-1

Upstream product

• 15475-27-1 potassium diphenylphosphine 
• 229485-69-2 (S)-[-2,2-dimethyl-1-[[[(4-methylphenyl)sulfonyl]oxy]methyl]propyl]carbamic acid 1,1-dimethylethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 112245-13-3 (S)-tert-leucinol 
• 153645-26-2 N-Boc-L-tert-leucinol 
• 1206227-45-3 (4S)-4-tert-butyl-1,2,3-oxathiazolidine-3-carboxylic acid 1,1-dimethylethyl ester 2,2-dioxide 
• 862120-57-8 (S)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutyl methanesulfonate 

Downstream Products

• 286454-86-2 (S)‐1‐(diphenylphosphino)‐3,3‐dimethylbutan‐2‐amine 

Relevant academic research and scientific papers

Asymmetric kinetic resolution of sulfides for the construction of unsymmetric sulfides and chiral 3,3-disubstituted oxindoles

A range of 3,3-disubstituted oxindoles accessed using para-quinone methides derived from isatins with thiols were used for the formation of unsymmetrical disulfides, and 3,3-disubstituted oxindoles with a chiral quaternary carbon center and unsymmetric di

Tunable Bifunctional Phosphine-Squaramide Promoted Morita-Baylis-Hillman Reaction of N-Alkyl Isatins with Acrylates

A series of highly tunable bifunctional phosphine-squaramide H-bond donor organocatalysts 6 has been synthesized from inexpensive and commercially available β-amino alcohols in moderate yields. Catalyst 6 can efficiently promote the asymmetric Morita-Baylis-Hillman (MBH) reaction of N-alkyl isatins with acrylate esters providing the chiral 3-substituted 3-hydroxy-2-oxindoles in good yields and enantioselectivities (up to 93 yield and 95 ee), in which the challenging substrate tert-butyl acrylate 9d, provided the best ee value to date. Moreover, this methodology was applied successfully in the synthesis of chiral cyclic spiropyrrolizidineoxindole and γ-butyrolactone derivatives without enantioselectivity deterioration. The possible mechanism of this MBH reaction was also investigated by 31PNMR, ESI-MS and KIE studies. The KIE experiments show that the electrophilic addition of N-methyl isatin to the complex of acrylate ester and phophine-squaramide is the rate-determing step of the asymmetric MBH reaction.

Asymmetrie [3+2] cycloadditions of allenoates and dual activated olefins catalyzed by simple bifunctional N-acyl aminophosphines

(Figure Presented) Bifunctional catalyst: Simple bifunctional N-Acyl aminophosphines such as 1 were developed to catalyze the first asymmetric [3+2] cycloaddition between allenoates and dual activated olefins. The cycloaddi- tion reactions afford multifun

Synthesis of chiral aminophosphines from chiral aminoalcohols via cyclic sulfamidates

(Chemical Equation Presented) Protic aminophosphines with multiple chiral centers were synthesized in good yields and high purity by the nucleophilic ring-opening of N-protected cyclic sulfamidates with metal phosphides, followed by hydrolysis and deprote

Versatile chiral bidentate ligands derived from α-amino acids: Synthetic applications and mechanistic considerations in the palladium- mediated asymmetric allylic substitutions

A new class of chiral amidine-phosphine hybrid ligands 7a,b, which are readily accessible from the corresponding α-amino acids, were developed. A versatility for construction of new ligands is desirable, by which a variety of reactions and substrates become applicable. Indeed, a variety of modifications, such as exchange reactions to other amino groups in the amidine skeleton and the production of other types of ligands, are possible using the precursor compounds of 7a. Thus, novel chiral ligands 7c,d, 8, 11, and 13, which provide sterically and electronically different chiral circumstances, were prepared and used for the palladium-mediated asymmetric allylic substitutions of both acyclic and cyclic compounds. In these reactions, high levels of asymmetric induction were achieved for both substrates. A marked advancement of reactivity and enantioselectivity in palladium-catalyzed asymmetric allylations of 1,3-diphenylpropen-2-yl pivalate 14a was attained by examination of electronic substituent effects in a new series of chiral P-N and S-N hybrid ligands 8 and 11. Mechanistic views concerning the enantiodiscriminating step were demonstrated, in which a good correlation between a novel Pr/Mr concept and the absolute configuration of allylation products are discussed for the prediction of enantioselecting direction. The use of ketene silyl acetals as nucleophiles was investigated and compared with the corresponding harder anionic carbon nucleophiles. The former nucleophiles afforded higher enantioselectivity in asymmetric allylic transformations of 14a.