90288-82-7

Upstream product

• 38053-91-7 2-trimethylsilyloxy-1,3-butadiene 
• 6832-16-2 methyl diazoacetate 

Downstream Products

• 116842-36-5 (1S,2S)-1-But-3-enyl-2-trimethylsilanyloxy-2-vinyl-cyclopropanecarboxylic acid methyl ester 
• 116842-36-5 Methyl 1-(3-Butenyl)-t-2-(trimethylsiloxy)-c-2-vinyl-r-1-cyclopropanecarboxylate 
• 86532-06-1 rac-Norbisabolid 
• 148429-39-4 2-(3-Methoxybenzyl)-6-(1-methyl-2,5-dioxocyclopentyl)-4-oxohexancarbonsaeure-methylester 
• 99377-03-4 methyl 4-oxo-6-phenylsulfanyl-hexanoate 
• 106799-46-6 4-Oxo-4-(4-oxocyclohexyl)butansaeure-methylester 
• 99377-06-7 methyl 4-oxo-6-(phenylsulfonyl)hexanoate 

Relevant academic research and scientific papers

Synthesis of Optically Active Siloxycyclopropanes by Asymmetric Catalysis, II. - Influence of the Silyl Enol Ether Structure on the Enantioselective Cyclopropanation with Methyl Diazoacetate

On the basis of reactions of (Z)-1-phenyl-1-(trimethylsiloxy)-1-propene (1a) with methyl diazoacetate (2) in the presence of different chiral (Schiff base) copper catalysts 4-Cu we extended our study of the silyl enol ethers 1b-1j.The highest enantiomeric excesses were obtained in most cases with catalyst 4b-Cu.Whereas cyclopropanations of 1-aryl- and 1-alkenyl-substituted silyl enol ethers 1b-1h gave moderate to good enantioselectivities (up to 80percent ee), alkyl-substituted olefins 1i and 1j provided less satisfactory results.By deprotonation and alkylation of 3c, 3h, and 3i it could be established that for these cyclopropanes the predominating absolute configuration of cis- and trans-cyclopropanes is equal at C-1, but consequently opposite at C-2.The influence of the silyl enol ether structure on the enantioselectivities achieved is briefly discussed. - Key Words: 2-Siloxycyclopropanecarboxylates / Silyl enol ethers / Cycloaddition / Asymmetric catalysis / (Schiff base)copper complexes, chiral

2-Alkenyl-Substituted Methyl 2-Siloxycyclopropanecarboxylates as Masked Vinyl Ketones: Efficient Syntheses of Highly Functionalized Michael Adducts.

2-Alkenyl-substituted methyl 2-siloxycyclopropanecarboxylates 3a, 3b, and 6 - easily available from the corresponding silyl enol ether - react with a variety of O-, N-, S-, and C-nucleophiles under mild acidic or basic conditions providing polyfunctionalized products 7-19 in good to excellent yields via 1,4-addition to vinyl ketones formed in situ.Due to the versatility of the nitro group, nitroalakne, adducts 15-19 are of special interest for further transformations.