144115-87-7

Upstream product

• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 1611465-69-0 (2E)-methyl-2-(benzyloxymethyl)pent-2-enoate 
• 153996-40-8 methyl (2E)-2-(hydroxymethyl)pent-2-enoate 
• 144115-85-5 1-(2-tetrahydropyranyloxy)-2-(2-tetrahydropyranyloxymethyl)-2-pentene 
• 100-39-0 benzyl bromide 
• 144115-51-5 2-propylidene-1,3-propanediol 

Downstream Products

• 1611465-55-4 (4S,5S,6S)-5-(benzyloxymethyl)-5,6-epoxyoct-1-en-4-ol 
• 1611466-91-1 (4R,5S,6S)-5-(benzyloxymethyl)-5,6-epoxyoct-1-en-4-ol 
• 1611465-51-0 (2S,3S)-2,3-epoxy-2-(benzyloxymethyl)pentanal 
• 1611465-75-8 (4S,5S)-5-(benzyloxymethyl)oct-1-en-4,5-diol 
• 144116-01-8 [(E)-4-Benzyloxymethyl-2-(3-[1,3]dioxolan-2-yl-propyl)-3-ethyl-penta-1,4-dienyl]-trimethyl-silane 
• 144116-02-9 [(1E,4E)-4-Benzyloxymethyl-2-(3-[1,3]dioxolan-2-yl-propyl)-hepta-1,4-dienyl]-trimethyl-silane 
• 144136-75-4 4-(benzyloxymethyl)-2-(4-chlorobutyl)-1-(trimethylsilyl)-1,4-heptadiene 
• 144136-74-3 2-(4-chlorobutyl)-3-ethyl-4-(benzyloxymethyl)-1-(trimethylsilyl)-1,4-pentadiene 
• 144115-95-7 2-butyl-4-(benzyloxymethyl)-1-(trimethylsilyl)-1,4-heptadiene 
• 144115-94-6 2-butyl-3-ethyl-4-(benzyloxymethyl)-1-(trimethylsilyl)-1,4-pentadiene 
• 144115-90-2 1-benzyloxy-2-(chloromethyl)-2-pentene 

Relevant academic research and scientific papers

Stereocontrol by quaternary centres: A stereoselective synthesis of (-)-luminacin D

Very high diastereoselectivity can be achieved by 1,3-chelation-controlled allylation of aldehydes that possess a non-chelating α-ether substituent, even if the α-position is a quaternary centre and/or a spiro-epoxide. This reaction was used as a key step in an enantioselective synthesis of the angiogenesis inhibitor luminacin D.

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.