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Usage

Uses

Used in Pharmaceutical Applications:
(S)-[(diphenyl)-t-butyldimethylsiloxymethyl]pyrrolidine is used as a key intermediate in the synthesis of potential drug candidates due to its unique structure and properties. Its chiral nature and specific functional groups enable the development of molecules with targeted therapeutic effects.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-[(diphenyl)-t-butyldimethylsiloxymethyl]pyrrolidine serves as a versatile building block for the creation of diverse molecules with specific functionalities. Its unique combination of a pyrrolidine ring, diphenyl, and a t-butyldimethylsiloxymethyl group allows for the synthesis of complex organic compounds with potential applications in various industries.
Used in Material Science:
(S)-[(diphenyl)-t-butyldimethylsiloxymethyl]pyrrolidine is used in the development of new materials and specialty polymers. Its unique structure and properties make it an interesting candidate for the creation of innovative materials with specific characteristics, such as improved stability, reactivity, or selectivity.
Used in Chemical Research:
(S)-[(diphenyl)-t-butyldimethylsiloxymethyl]pyrrolidine is utilized in chemical research to explore its properties and potential applications. Its chiral nature and unique structure provide opportunities for studying the effects of stereochemistry on reactivity and selectivity in various chemical reactions.

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 22348-32-9 (R)-α,α-diphenylprolinol 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 77581-28-3 (S)-proline-N-ethyl carbamate methyl ester 
• 100-58-3 phenylmagnesium bromide 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 22348-32-9 (S)-diphenylprolinol 

Relevant academic research and scientific papers

Enantioselective Construction of Spirooxindole-Fused Cyclopentanes

The present study reports an asymmetric organocatalytic cascade reaction of oxindole derivates with α,β-unsaturated aldehydes efficiently catalyzed by simple chiral secondary amine. Spirooxindole-fused cyclopentanes were produced in excellent isolated yields (up to 98%) with excellent enantiopurities (up to 99% ee) and moderate to high diastereoselectivities. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spiro compounds. In addition, a study showing the promising biological activity of selected enantioenriched products was accomplished.

Enantioselective Synthesis of N-Alkylamines through β-Amino C-H Functionalization Promoted by Cooperative Actions of B(C6F5)3and a Chiral Lewis Acid Co-Catalyst

We disclose a catalytic method for β-C(sp3)-H functionalization of N-alkylamines for the synthesis of enantiomerically enriched β-substituted amines, entities prevalent in pharmaceutical compounds and used to generate different families of chiral catalysts. We demonstrate that a catalyst system comprising of seemingly competitive Lewis acids, B(C6F5)3, and a chiral Mg- or Sc-based complex, promotes the highly enantioselective union of N-alkylamines and α,β-unsaturated compounds. An array of δ-amino carbonyl compounds was synthesized under redox-neutral conditions by enantioselective reaction of a N-alkylamine-derived enamine and an electrophile activated by the chiral Lewis acid co-catalyst. The utility of the approach is highlighted by late-stage β-C-H functionalization of bioactive amines. Investigations in regard to the mechanistic nuances of the catalytic processes are described.

KAHA ligations that form aspartyl aldehyde residues as synthetic handles for protein modification and purification

Aldehydes are widely recognized as valuable synthetic handles for the chemoselective manipulation of peptides and proteins. In this report, we show that peptides and small proteins containing the aspartic acid semialdehyde (Asa) side chain can be easily p

Enantioselective michael addition to α,β-Unsaturated aldehydes: Combinatorial catalyst preparation and screening, reaction optimization and mechanistic studies

Shortcut to chiral catalysts: An efficient combinatorial strategy based on back reaction screening by ESI-MS allows rapid evaluation of organocatalysis for the asymmetric Michael addition to α,β-unsaturated aldehydes (see scheme). An unexpected nonlinear effect has been observed in this reaction, resulting from a double nucleophilic-electrophilic activation mechanism involving two catalyst molecules "Chemical Equation Presented"

Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes

(Chemical Equation Presented) The direct, catalytic, asymmetric Michael addition of aldehydes to nitroolefins in the presence of a chiral diphenylprolinol silyl ether organocatalyst is described (see scheme). The desired 1,4-addition products were obtaine