52497-56-0

Upstream product

• 934-56-5 trimethyl(phenyl)stannane 
• 1838-94-4 isoprene epoxide 
• 960-16-7 tributylphenylstannane 
• 591-51-5 phenyllithium 
• 36219-40-6 1-bromo-2-hydroxy-2-methyl-3-butene 
• 917-54-4 methyllithium 
• 75593-21-4 2-methyl-3-phenylsulphinyl-4-phenylbut-1-ene 
• 443287-93-2 (Z)-methyl 2-methyl-3-trimethylsilyl-4-phenyl-2-butenoate 
• 14182-67-3 2-methyl-4-phenyl-but-2-enoic acid ethyl ester 
• 96548-13-9 4-methyl-4-vinyl-1,3-dioxolan-2-one 
• 98-80-6 phenylboronic acid 
• 98713-50-9 2-methyl-4-phenyl-3-phenylthiobut-1-ene 
• 665004-92-2 (Z)-2-methyl-3-trimethylsilyl-4-phenyl-2-butenoic acid 
• 56583-94-9 (phenylacetyl)trimethylsilane 

Downstream Products

• 55177-36-1 (2E)-2-methyl-4-phenylbut-2-enal 
• 153831-77-7 ((2R,3R)-3-benzyl-2-methyloxiran-2-yl)methanol 

Relevant academic research and scientific papers

Cross-coupling of vinylethylene carbonates with arylboronic acids catalyzed by in situ generated palladium nanoparticles in water

A practical and greener method of the cross-coupling of vinylethylene carbonates (VECs) with arylboronic acids has been described. The coupling reaction was catalyzed by in situ generated palladium nanoparticles (PdNPs) without any ligands and additional stabilizers in water under ambient conditions to provide useful 4-hydroxylprenylarenes and their derivatives in good to high yields.

Vanadium-catalyzed asymmetric epoxidation of allylic alcohols in water

Asymmetric V-catalyzed epoxidation of allylic alcohols can be carried out in water with chiral ligands, which incorporate sulfonamide and hydroxamic acid fragments. Furthermore, the reaction, notorious for its ligand-deceleration effect, in water turned into the ligand-accelerated process. By using this aqueous protocol, a range of allylic alcohols were epoxidized with up to 94% ee.

Convergent synthesis of (2R,3R,8R,9R)-N-Boc-ADDA

(Figure Presented) The convergent synthesis of N-Boc-(2R,3R,8R,9R,4E,6E)-3- amino-9-methoxy-2,6,8-trimethyl-10-phenyldecadenoic acid (enantio-N-Boc-ADDA) is reported. Our flexible approach takes advantage of highly efficient non-aldol aldol and cross-metathesis methodologies.

The first general method for Z-selective olefination of acylsilanes via ynolate anions providing multisubstituted alkenes

We have developed the first general method for a stereoselective olefination of acylsilanes via ynolate anions to produce (Z)-ss-silyl-α,β-unsaturated ester, which leads to tri- and tetrasubstituted alkenes. Copyright

Stereospecific synthesis of aldols

Methods are provided for preparing all four diastereomers of 2-alkyl-3-hydroxyalkanals, 2-alkyl-3-silyloxyalkanals, and the like, with high enantiocontrol, using non-aldol chemistry. The synthetic methods also provide novel, stereospecific routes to polyp

Tosylated lithium 2-(lithiomethyl)-2-propen-1-olate: A γ-alkoxide allyl sulfone anion in organic synthesis

Dilithiated 2-(tosylmethyl)-2-propen-1-ol (6) functioned as a nucleophile at the α-position of the allylic anion in reactions with deuterium oxide, alkyl halides, and aldehydes, and in conjugate additions to α,β-unsaturated carbonyl compounds. With nitro-

PALLADIUM CATALYZED COUPLING OF ORGANOSTANNANES WITH VINYL EPOXIDES

The coupling reaction of organotin reagents with vinyl epoxides, catalyzed by palladium, takes place at ambient temperatures, regioselectively, giving predominately the 1,4-addition product.Both aryl- and vinylstannanes undergo coupling in high yields, wh

FACILE SYNTHESIS OF (E)-ALLYLIC ALCOHOLS BY ACID-CATALYZED MODIFICATION OF THE MISLOW-EVANS REARRANGEMENT OF ALLYLIC SULFOXIDES

The Mislow-Evans rearrangement of α,β- and α,γ-disubstituted allylic sulfoxides (2) to (E)-allylic alcohols (4) was found to occur under acidic conditions.By combination of this method with a catalytic oxidation of allylic sulfides (1), a novel one-pot tr

Transition-metal-catalyzed Grignard Reaction of Isoprene Bromohydrin

The coupling reaction of isoprene bromohydrin with aryl and alkyl Grignard reagents catalyzed by tetrakis(triphenylphosphine)palladium(0) selectively gave the vinyl-group-migrated products.

Substitution Reactions of Secondary Halides and Epoxides with Higher Order, Mixed Organocuprates, R2Cu(CN)Li2: Synthetic, Stereochemical, and Mechanistic Aspects

Higher order cuprates, represented by the general formula R2Cu(CN)Li2, are readily prepared from copper cyanide and 2 equiv of an organolithium.These novel reagents react readily and efficiently with secondary unactivated iodides and bromides affording products of substitution.Likewise, mono-, di-, and trisubstituted epoxides undergo ring opening leading to the corresponding alcohols in excellent yields.The effects of solvent, temperature, gegenion, and variations in ligands are discussed.Replacement of the second equivalent of RLi by CH3Li strongly encouragestransfer of R over CH3 in R(CH3)Cu(CN)Li2 with halides.Use of PhLi as RRLi in place of one RTLi (i.e.RT(Ph)Cu(CN)Li2) is suggested for oxirane cleavage.The stereochemical implications associated with both couplings are also addressed.