168271-83-8

Upstream product

• 762-72-1 allyl-trimethyl-silane 
• 64286-85-7 N-(benzyloxycarbonyl)-L-phenylalanine allyl ester 
• 1161-13-3 N-Cbz-L-Phe 
• 122-78-1 phenylacetaldehyde 
• 621-84-1 O-benzyl carbamate 
• 4255-23-6 aletamine 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 168271-84-9 (1-Benzyl-but-3-enyl)-ethoxymethyl-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Remarkably mild and efficient catalytic Sakurai reaction of N-alkoxycarbonylamino sulfones with allyltrimethylsilane using indium(III) chloride

The Sakurai reaction of N-alkoxycarbonylamino sulfones with allyltrimethylsilane in the presence of a catalytic amount of indium(III) chloride at room temperature produces the corresponding protected homoallylic amines in high yields.

Dual Catalytic Decarboxylative Allylations of α-Amino Acids and Their Divergent Mechanisms

The room temperature radical decarboxylative allylation of N-protected α-amino acids and esters has been accomplished via a combination of palladium and photoredox catalysis to provide homoallylic amines. Mechanistic investigations revealed that the stability of the α-amino radical, which is formed by decarboxylation, dictates the predominant reaction pathway between competing mechanisms.

Re2O7-catalyzed three-component synthesis of protected secondary and tertiary homoallylic amines

Three-component synthesis of protected secondary and "for the first time" tertiary homoallylic amines is achieved from carbonyl, carbamate, and allyltrimethylsilanes using a Re2O7-catalyst under mild and open flask conditions. Excellent chemoselectivities and diastereoselectivities were observed.

A detailed investigation of the aza-prins reaction

The development of a Lewis acid-promoted aza-Prins reaction to form piperidines and pyrrolidines is described. Indium trichloride has been found to be a highly successful and mild Lewis acid for promoting this reaction. A thorough mechanistic investigation is described, including the factors that influence the formation of the 5- or 6-membered ring product(s). The Royal Society of Chemistry.

Bismuth triflate-catalyzed addition of allylsilanes to N- alkoxycarbonylamino sulfones: Convenient access to 3-Cbz-protected cyclohexenylamines

Bismuth triflate was found to be an efficient catalyst in the Sakurai reaction of allyltrimethylsilanes with N-alkoxycarbonylamino sulfones. The reaction proceeded smoothly with a low catalyst loading of Bi(OTf) 3·4H2O (2-5 mol%) to afford the corresponding protected homoallylic amines in very good yields (up to 96%). A sequential allylation reaction followed by ring-closing metathesis delivers 6-8 membered 3-Cbz-protected cycloalkenylamines.

The first catalytic Sakurai reaction of N-alkoxycarbonylamino sulfones with allyltrimethylsilane

The first Sakurai reaction of N-benzyloxycarbonylamino sulfones with allyltrimethysilane in the presence of a catalytic amount of Bi(OTf) 3.4H2O was investigated. Several solvents were screened for the Sakurai reaction and N-benzylox

Three-component synthesis of homoallylic carbamates

Scandium inflate catalyzed three component condensation of aldehyde, benzyl carbamate, and allyltrimethylsilane to afford the corresponding N-Cbz protected homoallylic amine is described. Copyright Taylor & Francis, Inc.

Iodine as a very powerful catalyst for three-component synthesis of protected homoallylic amines

Iodine catalyzes efficiently the three-component condensation of aldehydes, benzyl carbamate, and allyltrimethylsilane to afford the corresponding protected homo-allylic amines in excellent yields.

One-pot synthesis of protected homoallyl amines

An efficient one-pot procedure for the synthesis of protected homoallyl amines from aldehydes or aldehyde acetals, carbamates and allyltrimethylsilane under influence of borontrifluoride etherate was developed. Scope and limitations of the aldehyde and carbamate components are reported.

SAR of 2-benzyl-4-aminopiperidines NK1 antagonists. Part 2. Synthesis of CGP 49823

CGP 49823 is a potent NK1 antagonist which is centrally active after oral administration. The SAR of the C-2 substituent was investigated with respect to the affinity to the NK1 receptor. A practical synthesis of CGP 49823, suitable for scale-up, was developed. The key-step, a tandem acyliminium ion cyclization/Ritter reaction, gave trans-2-benzyl-4-acetamido-piperidines with high diastereoselectivity.