152668-35-4

Upstream product

• 2133-40-6 L-proline methyl ester monohydrochloride 
• 106-95-6 allyl bromide 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 147-85-3 L-proline 
• 591-87-7 Allyl acetate 

Downstream Products

• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 183155-28-4 methyl 1-allyl-1H-pyrrole-2-carboxylate 
• 1026390-17-9 (R)-1-((S)-2-Benzyloxymethyl-pyrrolidin-1-yl)-2-[(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-(2,2-diethoxy-ethyl)-amino]-pent-4-en-1-one 
• 1026152-96-4 [(R)-1-((S)-2-Benzyloxymethyl-pyrrolidine-1-carbonyl)-but-3-enyl]-(2,2-diethoxy-ethyl)-carbamic acid tert-butyl ester 
• 210347-80-1 (S)-1-allyl-2-(benzyloxymethyl)pyrrolidine 

Relevant academic research and scientific papers

Catalyst- and Base-Free Asymmetric Synthesis of Functionalized Prolines via One-Pot Cascade Reactions

A one pot, three-step cascade reaction to provide functionalized proline derivatives was developed. The Michael addition reaction of N-allylated proline and activated alkyne forms a zwitterionic intermediate that further undergoes cyclization and [2,3]-re

A short and concise synthetic route to (-)-coniceine

(-)-Coniceine, the simplest framework of indolizidine alkaloids, has been successfully accessed using a route in which ruthenium-catalyzed ring-closing olefin metathesis (RCM) was the key reaction to establish the unsaturated bicyclic lactam system.

A transition metal-catalyzed enyne metathesis for the preparation of pyrrolizidine alkaloid core: Application towards the total synthesis of stemaphylline

In this paper, we disclose an efficient route for the synthesis of pyrrolizidine alkaloid core and its application towards the total synthesis of stemaphylline. The key pyrrolizidine core was achieved with Ru-carbene catalyzed ring closing enyne metathesis (RCEM). The effect of different types and amounts of Ru-carbene catalysts, solvents and temperature were systematically studied. The advantage of this method includes the construction of pyrrolizidine alkaloid core in a single operation.

SPIRO-SULFONAMIDE DERIVATIVES AS INHIBITORS OF MYELOID CELL LEUKEMIA-1 (MCL-1) PROTEIN

The disclosure is directed to compounds of Formula I (I) Pharmaceutical compositions comprising compounds of Formula I as well as methods of their use and preparation, are also described.

Synthesis of chiral triazine coupling reagents based on esters of n-alkylproline and their application in the enantioselective incorporation of d or l amino acid residue directly from racemic substrate

Esters of N-methylproline and N-allylproline were prepared and used as component for synthesis of chiral triazine based coupling reagents. N-Triazinylammonium tetrafluoroborate obtained from methylester of L-N-methylproline, 2-chloro-4,6-dimethozxy-1,3,5-

Palladium nanoparticle-catalyzed C-N bond formation. A highly regio- and stereoselective allylic amination by allyl acetates

(Chemical Equation Presented) Palladium nanoparticles, generated in situ from the reaction of palladium(II) chloride, have been demonstrated to be an efficient catalyst for C-N bond formation. A variety of aliphatic and aromatic amines have been allylated by substituted and unsubstituted allyl acetates in high yields by using palladium nanoparticles in the presence of a base without any ligand. The allylations are highly regio- and stereoselective.

Synthesis and derivatization of substituted (R)- and (S)-C-allylglycines

Various (R)- and (S)-C-allylglycine derivatives were synthesized by means of an auxiliary controlled diastereoselective aza-Claisen rearrangement. Starting from (S)-configured auxiliaries derived from optically active proline, an aza-Claisen rearrangement enabled us to synthesize α(R)-configured γ,δ-unsaturated amides. Since (R)-allylglycine derivatives could be directly generated by reacting N-allylproline derivatives and various protected glycine fluorides, the corresponding (S)-enantiomers were built-up via an initial α-chloroacetyl chloride rearrangement and a subsequent chloride azide substitution with complete inversion of the configuration. High diastereoselectivities were obtained (>15:1). The auxiliary could be efficiently removed by organolithium reactions of the amides furnishing α-amino ketones. Another allyllithium addition allowed us to introduce a second allyl chain with high diastereoselectivity. Final ring closures by means of metatheses using Grubbs' (1) catalyst gave raise to the formation of enantiopure phenanthridines and cyclohexenes displaying defined substitution patterns ready for alkaloid total syntheses.

Synthesis of optically active C-allylglycine derivatives and conversion into isoquinolones

C-Allylglycyl amides can be efficiently synthesized via an auxiliary controlled diastereoselective aza-Claisen rearrangement. The stereodirecting unit is placed on an auxiliary derived from commercially available (S)-proline. After N-allylation, the obtained optically active allylamines were reacted with various N-protected glycyl fluorides to give the (2R)-C-allylglycyl amides in good yields. The diastereoselectivity of the asymmetric allylation varied between 1:1 and > 1:15 depending on the N-protective group, the auxiliary, and the reaction temperature. Likewise, the C-allylglycine derivatives can be used as monomers in peptide synthesis to synthesize (R)-proline derivatives or chiral isoquinolones; the latter should serve as building blocks in the total syntheses of alkaloids.

?-Allyl palladium methodology for selective deprotection of allylamines. Practical synthesis of secondary amines

The palladium-promoted deallylation of allylamines derived from primary and secondary amines is achieved with high to quantitative yield in the presence of 2-mercaptobenzoic acid as an allyl scavenger.This method was used for the sequential cleavage of diallylamines.A synthetic application of this procedure is presented in the preparation of secondary amines from diallylamines. - Keywords: allylamine; deallylation; sequential deprotection; ?-allyl palladium complexes; 2-mercaptobenzoic acid; substitution of amines

Intramolecular Nucleophilic Acyl Substitution Reactions of Halo-Substituted Esters and Lactones. New Applications of Organosamarium Reagents

Intramolecular nucleophilic acyl substitution reactions involving a broad range of halo substituted carboxylic acid derivatives have been accomplished in excellent yield employing samarium(II) iodide as the reductive coupling agent.Although particular substrates cyclized most effectively in THF in the presence of tripiperidinophosphine oxide, carboxylic acid esters, the focus of this report, cyclize equally well without such an additive in the presence of a catalytic quantity of iron(III) complexes.Thus a comprehensive series of halo substituted esters were cyclized in excellent yield to the corresponding 4-, 5-, and 6 -membered carbocycles.The reaction is extremely mild and selective as demonstrated by experiments wherein alkyl chlorides, acetals, and olefins remain completely intact under the reaction conditions.In addition to introducing a convenient procedure for preparing stereodefined spirocyclic systems, a new ring expansion sequence has been developed that appears extremely general for the preparation of various ring systems.