81112-87-0

Upstream product

• 108-94-1 cyclohexanone 
• 121896-38-6 2-tert-butyldimethylsilyloxyfuran 
• 61550-02-5 (furan-2-yloxy)-trimethylsilane 

Downstream Products

• 81112-94-9 5-cyclohexylidene-2(5H)furanone 

Relevant academic research and scientific papers

Diastereoselective synthesis of γ-butenolides catalyzed by potassium tert-butoxide

Potassium tert-butoxide (0.1 mol%) catalyzed a vinylogous Mukaiyama aldol reaction between aromatic and aliphatic aldehydes with 2-(trimethylsilyloxy) furan. The corresponding γ-butenolides were obtained in good yields with good diastereoselectivities. Copyright Taylor & Francis Group, LLC.

Diastereoselective Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan catalyzed by bismuth triflate

(Chemical Equation Presented) We have developed an efficient vinylogous Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan with various aromatic aldehydes mediated by bismuth triflate in low catalyst loading (1 mol %). The reaction proceeds rapidly and affords the corresponding 5-(hydroxy(aryl)methyl) furan-2(5H)-ones in high yields with good to very good diastereoselectivities (dr up to >98:2). Such selectivities, albeit previously reported with other Lewis acids, could this time be achieved with a much lower catalyst loading. 5-(Hydroxy(alkyl)methyl)furan-2(5H)-ones derived from ketones could also be obtained with good diastereoselectivities.

Bis(trifluoromethanesulfonyl)ethyl-bearing compound and acid catalyst, and method for preparing same

A bis(trifluoromethanesulfonyl)ethyl group-bearing compound represented by the following formula [1], [2] or [3] .

An effective method to introduce carbon acid functionality: 2,2-bis(trifluoromethanesulfonyl)ethylation reaction of arenes

Introducing strong acids: The reaction of electron-rich arenes with Tf 2CHCH2CHTf2 (Tf=trifluoromethanesulfonyl; triflyl) smoothly gave 2,2-bis(triflyl)ethylated arenes. This reaction provides a convenient methodology for the introduction of a Tf2CH group, which is known to be a strongly Bronsted acidic functionality, to organic compounds in a regioselective manner (see scheme). On the basis of this reaction, significantly active and thermally stable carbon acid catalysts were developed.

Carbon acid induced mukaiyama aldol type reaction of sterically hindered ketones

(Figure presented) 1,1,3,3-Tetrakis(trifluoromethanesulfonyl)propane (Tf2CHCH2CHTf2) is one of the most effective Bronsted acid precatalysts for the Mukaiyama aldol type reactions of sterically hindered ketones. By using Tf2CHCH2CHTf 2 in a range from 0.5 to 2.0 mol %, the vinylogous Mukaiyama aldol reaction of α-substituted cyclohexanones with 2-silyloxyfurans smoothly proceeded to give the aldol products in excellent yield without the loss of diastereoselectivity. Under similar conditions, acyclic ketene silyl acetals also performed as nice nucleophiles toward sterically hindered ketones. These findings suggest that Tf2CHCH2CHTf2 induced Mukaiyama aldol type reactions can overcome the steric hindrance between reaction sites.

SYNTHESIS OF 4-YLIDENEBUTENOLIDES FROM 2-TRIMETHYLSILOXYFURAN

Dehydration or dealkoxylation of the reaction products of various aldehydes, ketones, and acetals with 2-trimethylsiloxyfuran gave corresponding 4-ylidenebutenolides in good to high overall yields.