73710-76-6

Upstream product

• 14593-43-2 benzyl allyl ether 
• 140-88-5 ethyl acrylate 
• 60656-87-3 benzyloxyacetoaldehyde 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 4341-76-8 Ethyl 2-butynoate 
• 100-51-6 benzyl alcohol 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 

Downstream Products

• 73710-77-7 4-Benzyloxymethyl-1H-pyrrole-3-carboxylic acid ethyl ester 
• 363165-99-5 4-(benzyloxyl)-but-2-enoic acid 
• 1393834-15-5 (4R,Z)-N-(4'-benzyloxy-but-3'-enoyl)-4,5,5-triphenyloxazolidin-2-one 
• 1393834-02-0 (2'S,4R,Z)-N-(4'-benzyloxyl-2-methylbut-3'-enoyl)-4,5,5-triphenyloxazolidin-2-one 
• 1393833-98-1 (2'R,4R,Z)-3-(4'-benzyloxyl-2'-allylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone 
• 1393834-03-1 (2'S,4R,Z)-3-(4'-benzyloxyl-2'-allylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone 
• 1393834-04-2 (2'S,4R,Z)-3-(4'-benzyloxyl-2'-benzylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone 
• 1393834-00-8 (2'R,4R,Z)-3-(4'-benzyloxyl-2'-benzylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone 
• 1393834-08-6 C₂₀H₂₇NO₄ 
• 1393833-94-7 (2'R,4R,Z)-N-(4'-benzyloxyl-2-methylbut-3'-enoyl)-4,5,5-triphenyloxazolidin-2-one 
• 1393834-09-7 C₂₂H₂₉NO₄ 
• 1393834-10-0 C₂₆H₃₁NO₄ 
• 1393834-13-3 (3R,5S)-5-(benzyloxy)-3-methyldihydrofuran-2-(3H)-one 
• 1393834-12-2 (3R,5R)-5-(benzyloxy)-3-methyldihidrofuran-2-(3H)-one 

Relevant academic research and scientific papers

Iridium-Catalyzed Regioselective Hydroalkynylation of Internal Alkenes Directed by an Oxime

We report here an iridium-catalyzed hydroalkynylation of allylic alcohols protected by an oxime group. Catalytic alkynylation occurs exclusively at the distal position of the alkene. This method generates γ-alkynyl alcohol oximes directly from internal alkenes and terminal alkynes. The oxime group can be readily removed to afford a free alcohol, thus providing an indirect route for the catalytic hydroalkynylation of allylic alcohols.

Diastereoselective alkylations of oxazolidinone vinylogous glycolates

A highly Z-selective isomerization (double bond migration) was observed when oxazolidinone vinylogous glycolate was exposed to a strong base to give N-acyl oxazolidinone, bearing an electron rich olefin. The corresponding enolate was exposed to alkyl halides to provide alkylated compounds on the γ-position with respect to OBn group, with high regioselectivity and moderate diastereoselectivity. However, the nature of the chiral oxazolidinone leads to a significant increase in the reaction diastereoselectivity. A stereospecific formation of cis-olefin was also observed in these alkylated compounds.

Synthesis of polysubstituted pyrroles

Cross coupling metathesis reactions from two ethylenic compounds 4 and 5 easily led to Michael acceptors 6ab and 7a-b. Reaction of these compounds, or of enone 5', with p-toluenesulfonylmethyl isocyanide (TosMIC) provided the disubstituted pyrroles 9a-c a

Synthesis of N-heterocycles, beta-amino acids, and allyl amines via aza-payne mediated reaction of ylides and hydroxy aziridines

An ylide-based aza-Payne rearrangement of 2,3-aziridin-1-ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under the basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring closure yields the desired pyrrolidine, thus completing the relay of the 3-membered the 5-membered nitrogen containing ring system. This process takes place with complete transfer of stereochemical fidelity, and can be applied to sterically hindered aziridinols.