113964-32-2

Upstream product

• 1871-57-4 2-chloromethyl-3-chloroprop-1-ene 
• 100-51-6 benzyl alcohol 
• 20194-18-7 sodium phenyl-methanolate 

Downstream Products

• 139747-92-5 (2-benzyloxymethyl-2-propenyl)trimethylsilane 
• 144115-80-0 5-(benzyloxymethyl)-3-(<1-(2)H1>-(trimethylsilyl)methylene)-5-hexen-1-ol 
• 66950-88-7 1-(3-hydroxy-2-methylene)propylcyclohexanol 
• 144115-81-1 <1-(2)H1>-4-(benzyloxymethyl)-2-(4-chlorobutyl)-1-(trimethylsilyl)-1,4-pentadiene 
• 144115-83-3 2-(6-(benzyloxymethyl)-4-(<1-(2)H1>-(trimethylsilyl)methylene)-6-heptenyl)-1,3-dioxolane 
• 175694-24-3 3-Benzyloxy-2-chloromethyl-propan-1-ol 
• 347886-00-4 [2-(bromomethyl)prop-2-en-1-yloxy]methylbenzene 
• 922523-30-6 C₁₅H₂₀O₂ 
• 922523-27-1 C₃₃H₃₈O₇ 
• 922523-31-7 C₃₄H₄₂O₈ 
• 922523-36-2 C₄₃H₆₂O₈Si 
• 922523-55-5 C₂₇H₄₆O₅Si 
• 922523-56-6 C₃₀H₅₄O₅Si₂ 
• 922523-57-7 C₂₉H₅₄O₄Si₂ 

Relevant academic research and scientific papers

One-Pot Twofold Unsymmetrical C-Si Bond 2,6-Bifunctionalization of Arenes via Sequential [1,4]-Csp2 to O-Silyl Migration

Twofold unsymmetrical C-Si bond bifunctionalization of 2,6-di(trimethylsilyl) benzyl alcohols has been achieved in one pot via sequential [1,4]-Csp2 to O-silyl migration. The hydroxyl group functions as an "on-off-on" switch to control two successive silyl migrations, and 4,7-dimethyl-o-phenanthroline ligand favors cleavage of the endocyclic C-Si bond. Diverse Csp3/Csp3 or Csp2/Csp3 electrophiles can be installed at the 2- and 6-positions. This approach was used to chemoselectively functionalize the three C-Si bonds of 2,4,6-tri(trimethylsilyl) benzyl alcohol, transforming it into isochroman derivatives. The approach even works as a five-component reaction to construct complex symmetric structures.

One-Pot Three-Component Synthesis of Vicinal Diamines via In Situ Aminal Formation and Carboamination

A synthesis of vicinal diamines via in situ aminal formation and carboamination of allyl amines is reported. Employing highly electron-poor trifluoromethyl aldimines in their stable hemiaminal form was key to enable both a fast and complete aminal formation as well as the palladium-catalyzed carboamination step. The conditions developed allow the introduction of a wide variety of alkynyl, vinyl, aryl, and hetereoaryl groups with complete regioselectivity and high diastereoselectivity. The reaction exhibits a high functional-group tolerance. Importantly, either nitrogen atom of the imidazolidine products can be selectively deprotected, while removal of the aminal tether can be achieved in a single step under mild conditions to reveal the free diamine. We expect that this work will promote the further use of mixed aminal tethers in organic synthesis.

Synthetic studies toward pectenotoxin 2. Part I. Stereocontrolled access to the C10-C22 fragment

(Chemical Equation Presented) A highly stereocontrolled and efficient synthesis for a fully functionalized C10-C22 fragment of pectenotoxin 2 Is described using a convergent sequence involving a stereoselective methylation of β-hydroxyketone as a key step.

Synthesis of the southern FGHI ring system of azaspiracid-1 and investigation into the controlling elements of C28- and C36-ketalization

Heading south: An efficient approach to the FGHI southern ring system of azaspiracid-1 is disclosed. Each of the eight stereogenic centers is generated with excellent diastereoselectivity. In addition, the stereochemical outcome of the ketalization steps could be controlled by careful selection of the conditions. Teoc = 2-(trimethylsilyl)ethoxycarbonyl; TMS = trimethylsilyl; TIPS = triisopropylsilyl; Bn = benzyl. (Chemical Equation Presented).

Design, synthesis and X-ray crystallographic studies of [7.3.1] and [8.3.1] macrocyclic FKBP-12 ligands

The design, synthesis, and structure activity relationships of a series of novel macrocyclic FKBP-12 ligands 1 are reported. The crystal structure of the complex between 7 and human FKBP-12 is reported and some SAR results are discussed based on this complex.

γ-Functionalised β-methylene organolithium compounds from 3-chloro-2-(chloromethyl)propene: Synthetic applications

The reaction of functionalised methallylic chlorides 1 with an excess of lithium powder and a catalytic amount of naphthalene (8 mol%) in the presence of a carbonyl compound (Barbier-type conditions) at -78°C leads, after hydrolysis with water, to the corresponding polyfunctionalised compounds 2. Starting materials 1 are easily available from 3-chloro-2-(chloromethyl)propene by nucleophilic substitution.

Allylmetallation of 1-Silylalkynes by 2-(Bromozincmethyl)-2-alkenyl Ethers followed by Pd(0)-catalyzed Cyclization: A one-pot Synthesis of 4-Methylenecyclopentenes

Reaction of 2-(bromozincmethyl)-2-alkenyl ethers 1 a,b,c,d with 1-(trimethylsilyl)-1-alkynes 2 afforded carbometallation products 3, which were converted by Pd(0)-catalyzed cyclization to 4-methylenecyclopentenes 5.The rates of both the addition and cyclization step depend on the concentration of the organozinc compound and the preparation of 5 is best performed using a 1,4-1,8 M solution of 1.At lower concentrations reaction times must be longer and, when 1c is reacted, the addition reaction is incomplete and gives rise to a mixture of products (3 and 14), which on Pd(0)-treatment leads to a mixture of isomeric methylenecyclopentenes (5, 15 and 16). - Key Words: alkyne addition; carbometallation; 2-alkenylzinc compounds; Pd(0)-catalysis; cyclopentenes.

β-Lactam antifungals. II. Enantiocontrolled synthesis of (2R,5S)-2-hydroxymethyl-1-carbapenam, the carba-analog of a clavam antifungal

(2R,5S)-2-Hydroxymethyl-1-carbapenam (3), the carba-analog of an antifungal β-lactam (2R,5S)-2-(hydroxymethyl)clavam (1), was synthesized in an enantiocontrolled manner, starting from the coupling reaction of an optically active phthalimido-acetate (3S,4S)-4 and an allylsilane 7, followed by removal of the phthalimido group that was crucial for asymmetric induction. Hydroboration, protecting-group interconversion, and cyclization gave 3 stereoselectively.

Propanol derivatives

Propanol derivatives of formula (I) wherein X is a leaving group; R1 is H or a protecting group; and R2 is H, and R3 is a group--CH2 Y wherein Y is a leaving group; or R2 and R3 together form =CH2. The propanol derivatives of the formula (I) are useful as multifunctional alkylating agents.