340129-94-4

Usage

Uses

Used in Organic Synthesis:
(R)-tert-butyl 2-vinylpyrrolidine-1-carboxylate is used as a building block for the synthesis of various organic compounds. Its unique structural features and reactivity make it a valuable intermediate in the creation of complex molecules.
Used in Pharmaceutical Research:
(R)-tert-butyl 2-vinylpyrrolidine-1-carboxylate is used as a key component in the development of new drugs. The pyrrolidine moiety, which is present in many biologically active molecules, allows for the design and synthesis of novel pharmaceuticals with potential therapeutic applications.
Used in the Development of New Materials:
(R)-tert-butyl 2-vinylpyrrolidine-1-carboxylate is used as a starting material for the creation of new materials with unique properties. Its structural features and reactivity enable the development of innovative materials for various applications, including but not limited to, the medical, chemical, and materials science industries.

Upstream product

• 593-60-2 Vinyl bromide 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 593-66-8 vinyliodide 
• 1353722-73-2 6-((tert-butoxycarbonyl)amino)-1-((tert-butyldimethylsilyl)oxy)hex-2-yne 
• 24424-99-5 di-tert-butyl dicarbonate 
• 128773-83-1 6-azidohex-2-yn-1-ol 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 105838-14-0 tert-butyl N-tosyloxycarbamate 
• 1353722-72-1 6-azido-1-((tert-butyldimethylsilyl)oxy)hex-2-yne 
• 959043-38-0 (Z)-6-((tert-butoxycarbonyl)amino)-1-((tert-butyldimethylsilyl)oxy)hex-2-ene 

Downstream Products

• 132482-06-5 tert-butyl (2R)-2-(2-hydroxyethyl)pyrrolidine-1-carboxylate 

Relevant academic research and scientific papers

Enantioselective Aza-Heck Cyclizations of N-(Tosyloxy)carbamates: Synthesis of Pyrrolidines and Piperidines

Pd(0)-systems modified with SPINOL-derived phosphoramidate ligands promote highly enantioselective aza-Heck cyclizations of alkenyl N-(tosyloxy)carbamates. The method provides versatile access to challenging N-heterocycles and represents the broadest scope enantioselective aza-Heck protocol developed to date.

Enantioselective synthesis of pyrrolidine-, Piperidine-, and azepane-type N -heterocycles with α-alkenyl substitution: The CpRu-catalyzed dehydrative intramolecular N -allylation approach

A cationic CpRu complex of chiral picolinic acid derivatives [(R)- or (S)-Cl-Naph-PyCOOCH2CH=CH2] catalyzes asymmetric intramolecular dehydrative N-allylation of N-substituted ω-amino- and -aminocarbonyl allylic alcohols with a substrate/catalyst ratio of up to 2000 to give α-alkenyl pyrrolidine-, piperidine-, and azepane-type N-heterocycles with an enantiomer ratio of up to >99:1. The wide range of applicable N-substitutions, including Boc, Cbz, Ac, Bz, acryloyl, crotonoyl, formyl, and Ts, significantly facilitates further manipulation toward natural product synthesis.

Copper mediated scalemic organolithium reagents in alkaloid syntheses

Scalemic 2-pyrrolidinylcuprates generated via asymmetric deprotonation of N-Boc-pyrrolidine followed by treatment with THF soluble CuCN·2LiCl react with ω-functionalized vinyl halides to afford 2-alkenyl-N-Boc- pyrrolidines. N-Boc deprotection and cyclization via intramolecular N-alkylation generates the pyrrolizidine or indolizidine skeletons. Subsequent functional group manipulation affords enantioenriched (+)-heliotridane, (+)-isoretronecanol, a formal synthesis of (+)-laburnine, (+)-(R)-2,3,5,7a- tetrahydro-1H-pyrrolizine, (R)-1,2,3,5,6,8a-hexahydroindolizine, (+)-ent-δ-coniceine, (+)-tashiromine and (+)-5-epitashiromine.

Reactivity and Enantioselectivity in the Reactions of Scalemic Stereogenic α-(N-Carbamoyl)alkylcuprates

Stereogenic 2-(N-carbamoyl)pyrrolidinylcuprates prepared from scalemic (i.e., enantioenriched) N-Boc-2-lithiopyrrolidine and THF soluble CuCN·2LiCl react with vinyl iodides, vinyl triflates, β-iodo-α,β-enoates, propargyl mesylates, and allyl bromide to afford the substitution products with excellent enantioselectivity. Excellent enantiomeric ratios are obtained in the conjugate addition reactions with methyl vinyl ketone while low enantiomeric ratios can be achieved with acrylate esters using HMPA/TMSCl activation. Enantiomeric ratios vary with substrate substitution patterns and the observed enantioselectivities appear to be more a function of cuprate-electrophile reactivities than of the reaction type (e.g., substitution, conjugate addition). Low enantiomeric ratios are obtained with the α-(N-carbamoyl)benzylcuprates. The lithium-copper transmetalation and cuprate vinylation reactions proceed with retention of configuration.