84782-98-9

Upstream product

• 84782-96-7 3-Benzyl-2-methyl-4-oxo-tetrahydro-thiophene-3-carboxylic acid methyl ester 
• 623-43-8 crotonic acid methyl ester 
• 100-39-0 benzyl bromide 
• 98837-36-6 methyl 3-hydroxy-2-methylenebutyrate 
• 71-43-2 benzene 
• 22787-68-4 methyl 2-(1-acetoxyethyl)acrylate 
• 98-80-6 phenylboronic acid 
• 65369-27-9 2-Methyl-4-oxo-tetrahydrothiophen-3-carbonsaeuremethylester 

Downstream Products

• 79140-86-6 (2E)-2-(phenylmethyl)-2-butenoic acid 

Relevant academic research and scientific papers

Rhodium-catalyzed formation of stereocontrolled trisubstituted alkenes from Baylis-Hillman adducts

We report here efficient and general conditions for the formation of stereodefined trisubstituted alkenes using the rhodium-catalyzed reaction of unactivated Baylis-Hillman adducts with either organoboronic acids and potassium trifluoro(organo)borates. Th

Access to stereodefined trisubstituted alkenes via rhodium-catalyzed 1,4-addition of potassium trifluoro(organo)borates to Baylis-Hillman adducts

In the presence of a rhodium catalyst, unactivated Baylis-Hillman adducts reacted regioselectively with potassium trifluoro(organo)borates to afford stereodefined trisubstituted alkenes with good yields. This highly efficient reaction (aerobic conditions,

Baylis-Hillman adducts in rhodium-catalyzed 1,4-additions: Unusual reactivity

In the presence of a rhodium catalyst, unactivated Baylis-Hillman adducts reacted with arylboronic acids to afford trisubstituted alkenes with good yields. This highly efficient reaction (aerobic conditions, low temperature) is believed to proceeds via an unexpected mechanism involving 1,4-addition/ β-hydroxy elimination steps and not π-allyl type rhodium intermediates.

The conjugate addition-aldol tandem reaction of α,β-unsaturated esters catalyzed by lithium benzenethiolate

Reactions of α,β-unsaturated esters with aldehydes were catalyzed by 0.2 equiv of lithium benzenethiolate in the presence of phenyl trimethylsilyl sulfide to afford the conjugate addition-aldol tandem reaction products in the anti stereoselectivity and go

The Friedel-Crafts reaction of the Baylis-Hillman adducts

A simple and convenient methodology for the stereoselective construction of 2-benzyl substituted trisubstituted olefins via sulfuric acid catalyzed Friedel-Crafts reaction of benzene with Baylis-Hillman adducts is described.

Applications of the Baylis-Hillman Reaction 2: a Simple Stereoselective Synthesis of (E)- and (Z)-Trisubstituted Alkenes

Reaction of Grignard reagents with methyl 3-acetoxy-2-methylenealkanoates produces (2E)-2-substituted alk-2-enoates, whereas a similar reaction with 3-acetoxy-2-methylenealkanenitriles provides (2Z)-2-substituted alk-2-enenitriles in high (Z)-stereoselectivity.

Stereoselective α-Alkylation of α,β-Unsaturated Esters Utilizing Conjugate Addition of Nitrogen Nucleophiles (R2NLi)

Treatment of α,β-unsaturated esters (1) with lithium amides i2 and LiN(CH2Ph)SiMe3> followed by alkylation and elimination of the amino groups produced trisubstituted enoates (2) with high stereoselectivity.

Methyl 4-Oxothiolane-3-carboxylate and Methyl 2-Methyl-4-oxothiolane-3-carboxylate Anions as Synthetic Equivalents of α-Acrylate and α-Crotonate Anions. Formal Synthesis of Integerrinecic Acid

The base-promoted fragmentation of the C-alkylation products (6a-h) and (8a-e) of methyl 4-oxothiolane-3-carboxylate (4) and methyl 2-methyl-4-oxothiolane-3-carboxylate (5) gave good yields of the α-substituted acrylates (7a-h) and α-substituted crotonate

A Novel α-Acrylate Anion Equivalent: A Useful Synthon for α-Substituted Acrylic Esters

An efficient preparation of α-substituted acrylic esters is described, based on the Dieckmann-Michael retrograde reactions of the C-alkylation products of 4-methoxycarbonylthiolan-3-one (1).