67488-65-7

Upstream product

• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 98-59-9 p-toluenesulfonyl chloride 
• 104830-31-1 N^α,N^δ-dinitroso-N^α,N^δ-ditosyl-L-ornithine methyl ester 
• 147-85-3 L-proline 
• 67-56-1 methanol 
• 51077-01-1 L-N-tosyl-proline 
• 70-26-8 L-ornithine 
• 2133-40-6 methyl pyrrolidine-2-carboxylate hydrochloride 
• 43041-12-9 methyl pyrrolidine-2-carboxylate 
• 675-20-7 piperidin-2-one 
• 23438-61-1 1-(toluene-4-sulfonyl)piperidin-2-one 
• 2133-40-6 L-proline methyl ester monohydrochloride 
• 95305-51-4 dimethyl (2S)-2-{[(4-methylphenyl)sulfonyl]amino}pentane-1,5-dioate 

Downstream Products

• 920323-94-0 N-(p-tosyl)proline N'-methylamide 
• 79659-73-7 N-<(4-Methylphenyl)sulfonyl>tryptophan Methyl Ester 
• 73-22-3 L-Tryptophan 
• 55456-48-9 ((2S)-1-p-toluenesulfonyl-2-pyrrolidinyl)methanol 
• 133111-29-2 5-(n-hexyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine 
• 86658-77-7 5-Methoxy-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester 
• 91645-35-1 (RS)-[1-(toluene-4-sulfonyl)-pyrrolidine-2-yl]-methanol 

Relevant academic research and scientific papers

Phenotypic Screening of Chemical Libraries Enriched by Molecular Docking to Multiple Targets Selected from Glioblastoma Genomic Data

Like most solid tumors, glioblastoma multiforme (GBM) harbors multiple overexpressed and mutated genes that affect several signaling pathways. Suppressing tumor growth of solid tumors like GBM without toxicity may be achieved by small molecules that selec

Heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis

A general and efficient method for heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis to access a wide range of structurally diverse oxygen as well as nitrogen heterocycles up to a gram scale is reported. The potential application of this new methodology is demonstrated by the total synthesis of (-)-codonopsinine and (+)-centrolobine. Herein it is proposed that selectfluor, unlike a fluorinating reagent, acts as an oxidative quencher and a hydrogen radical acceptor.

Chemoselective Intramolecular Formal Insertion Reaction of Rh–Nitrenes into an Amide Bond Over C?H Insertion

The past few decades have witnessed extensive efforts to disclose the unique reactivity of metal–nitrenes, because they could be a powerful synthetic tool for introducing the amine functionality into unactivated chemical bonds. The reactivity of metal–nitrenes, however, is currently mainly confined to aziridination (an insertion into a C=C bond) and C?H amination (an insertion into a C?H bond). Nitrene insertion into an amide C?N bond, however, has not been reported so far. In this work we have developed a rhodium-catalyzed one-nitrogen insertion into amide C?N and sulfonamide S?N bonds. Experimental and theoretical analyses based on density functional theory indicate that the formal amide insertion proceeds via a rhodium-coordinated ammonium ylide formed between the nitrene and the amide nitrogen, followed by acyl group transfer concomitant with C?N bond cleavage. Mechanistic studies have allowed rationalization of the origin of the chemoselectivity observed between the C?H and amide insertion reactions. The methodology presented herein is the first example of an insertion of nitrene into amide bonds and provides facile access to unique diazacyclic systems with an N?N bond linkage.

Preparation method of polysubstituted pyrrole compound

The invention discloses a preparation method of a polysubstituted pyrrole compound. The preparation method comprises steps as follows: an alkyne enamine compound is subjected to a cyclization reactionunder the catalytic action of univalent gold, a product

Synthesis of 2-carboxylated aza-ring derivatives through α-monohalogenation/ring-contraction of N-sulfonyl lactams

2-Carboxylated aza-rings have been synthesized in two steps through a highly selective monohalogenation of N-sulfonylated lactams of various ring sizes (from 5- to 8-membered rings) followed by a ring contraction reaction. The selective monohalogenation of N-sulfonyl lactams has been achieved in modest to excellent yields (9 examples, 39–96%) using N-halogenosuccinimides via the in situ generation of trimethylsilyl ketene aminal derivatives. The so-obtained α-halogeno N-sulfonyl lactams were engaged in a ring opening/ring closing reaction in the presence of various alcohols or anilines under basic conditions affording 2-carboxylated aza-rings, such as azetidine, pyrrolidine or piperidine derivatives in high yields (24 examples, 61–99%).

Highly stereoselective syntheses of proline-derived vicinal amino alcohols through grignard addition onto N-tosylprolinal

A highly diastereoselective Grignard addition to N-tosyl-l-prolinal has been developed to deliver a variety of proline-derived vicinal amino alcohols in good to excellent yields with high diastereoselectivities. A similar selectivity was also obtained by using N-tosyl-d-prolinal. The methodology has been applied to the synthesis of medicinally important 3-hydroxy-2-phenylpiperidines.

Gold(I)-Catalyzed N-Desulfonylative Amination versus N-to-O 1,5-Sulfonyl Migration: A Versatile Approach to 1-Azabicycloalkanes

Valuable 1-azabicycloalkane derivatives have been synthesized through a novel gold(I)-catalyzed desulfonylative cyclization strategy. An ammoniumation reaction of ynones substituted at the 1-position with an N-sulfonyl azacycle took place in the presence of a gold cation by intramolecular cyclization of the disubstituted sulfonamide moiety onto the triple bond. Depending on the size of the heterocyclic ring and substitution of the substrates, two unprecedented forms of nucleophilic attack on the sulfonyl group were exploited, that is, a N-desulfonylation in the presence of an external protic O nucleophile (37–87 %, 10 examples) and a unique N-to-O 1,5-sulfonyl migration (60–98 %, 9 examples).

Chemoselective Intramolecular Functionalization of Methyl Groups in Nonconstrained Molecules Promoted by N-Iodosulfonamides

Mechanistic evidence observed in Hofmann-L?ffler-Freytag-type reactions has been crucial to achieve the chemoselective functionalization of methyl groups under mild conditions. Radical-mediated methyl iodination and subsequent oxidative deiodination are the key steps in this functionalization, where iodine chemistry has a pivotal role on the formation of the C-N bond. The concepts of single hydrogen atom transfer (SHAT) and multiple hydrogen atom transfer (MHAT) are introduced to describe the observed chemoselectivity. (Chemical Equation Presented).

NAlkylation of tosylamides using esters as primary and tertiary alkyl sources: Mediated by hydrosilanes activated by a ruthenium catalyst

Select your group: Either a primary or tertiary alkyl group can be selectively introduced onto the nitrogen atom of tosylamides in a ruthenium-catalyzed reaction employing hydrosilanes through a judicious choice in the esters that serve as the alkyl source (see scheme; Ts= 4-toluenesulfonyl). These N-alkylation reactions are useful for construction of naturally occurring azacyclic skeletons. Copyright

Counterion-mediated hydrogen-bonding effects: Mechanistic study of gold(I)-catalyzed enantioselective hydroamination of allenes

Two of a kind: A new type of counterion-mediated syn-addition mechanism has been presented in gold-catalyzed enantioselective hydroamination reactions with [(R)-binap(AuOPNB)2] (OPNB=para-nitrobenzoate). A combination of both hydrogen bonding and the N-Au interaction efficiently controlled the challenging enantioselectivity of allenes.