120823-67-8

Upstream product

• 41108-81-0 tert-butyl (trimethylsilyl)acetate 
• 104-55-2 3-phenyl-propenal 
• 100-42-5 styrene 
• 1663-39-4 tert-Butyl acrylate 
• 10562-83-1 dihydro-<(E)-2-phenylethenyl>phosphonic acid 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 83947-56-2 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane 
• 67093-66-7 (E)-3-hydroxy-5-phenyl-pent-4-enoic acid tert-butyl ester 
• 14371-10-9 (E)-3-phenylpropenal 
• 120823-65-6 t-butyl (tri-n-butylstannyl)(trimethylgermyl)acetate 
• 86302-43-4 (tert-Butoxycarbonylmethylene)triphenylphosphorane 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 49653-47-6 tert-butyl 2,2-dichloroacetate 

Downstream Products

• 153498-44-3 Benzyl-{(E)-(S)-1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-phenyl-allyl}-((R)-1-phenyl-ethyl)-amine 
• 28010-12-0 5-phenylpenta-2,4-dienoic acid 
• 153498-39-6 (E)-(S)-3-[Benzyl-((R)-1-phenyl-ethyl)-amino]-5-phenyl-pent-4-enoic acid tert-butyl ester 

Relevant academic research and scientific papers

Mild and stereoconvergent palladium-catalyzed carbonyl alkenation reaction of α,β-unsaturated aldehydes

The addition of preformed ketone and ester enolates to α,β-unsaturated aldehydes 1 followed by in situ protection leads to the carbonates 3, 7, 8, 11, and 13. They are converted into sensitive functionalized dienes 4, 9, 12, and 14 by a smooth palladium-c

Asymmetric dehydration of β-hydroxy esters via kinetic resolution

Catalytic asymmetric dehydration of β-hydroxy esters via kinetic resolution has been investigated. The kinetic resolution of rac-β-hydroxy esters in the presence of prolinol chiral ligand 2a and BrZnCH2CO2t-Bu can provide highly enan

Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides

Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).

METHODS FOR PHOSPHINE OXIDE REDUCTION IN CATALYTIC WITTIG REACTIONS

A method for increasing the rate of phosphine oxide reduction, preferably during a Wittig reaction comprising use of an acid additive is provided. A room temperature catalytic Wittig reaction (CWR) the rate of reduction of the phosphine oxide is increased due to the addition of the acid additive is described. Furthermore, the extension of the CWR to semi-stabilized and non-stabilized ylides has been accomplished by utilization of a masked base and/or ylide-tuning.

Palladium(ii)-catalyzed cross-coupling of simple alkenes with acrylates: A direct approach to 1,3-dienes through C-H activation

The results from a direct palladium-catalyzed cross-coupling reaction between a variety of olefins with acrylate through vinylic C-H activation that give the corresponding butadienes in moderate to good yields and stereoselectivities are reported. Given the reaction's ability to tolerate a wide range of styrenes, aliphatic alkenes and acrylates, this atom- and step-economical methodology offers a straightforward method to forge new C-C bonds of the valuable diene products from readily available starting materials under very mild reaction conditions.

Breaking the ring through a room temperature catalytic wittig reaction

One ring no longer rules them all: Employment of 2.5-10 mol % of 4-nitrobenzoic acid with phenylsilane led to the development of a room temperature catalytic Wittig reaction (see scheme). Moreover, these enhanced reduction conditions also facilitated the use of acyclic phosphine oxides as catalysts for the first time. A series of alkenes were produced in moderate to high yield and selectivity. Copyright

Pd(II)-catalyzed dehydrogenative olefination of vinylic C-H bonds with allylic esters: General and selective access to linear 1,3-butadienes

This work demonstrates a general and efficient method to prepare conjugated dienes by Pd(II)-catalyzed direct olefination of unactivated alkenes with allylic esters and acrylates via vinylic C-H activation. Various aryl and heteroaryl alkenes as well as a

Stereoselective olefination reactions promoted by Rieke manganese

A study of the advantages of using manganese, an inexpensive and nontoxic metal, to perform stereoselective β-elimination reactions and to promote sequential olefination reactions of aldehydes to obtain α,β- unsaturated esters and amides is presented. Various elimination reactions, all of them characterized by occurring with complete stereoselectivity and in high yields, were performed using active manganese (Mn*) as metalating agent. This ability of manganese has been applied to develop a novel and direct synthesis of (E)-α,β-unsaturated esters or amides and (Z)-α,β-unsaturated α-halo esters and α-choroamides through a Mn*-mediated sequential olefination protocol of aldehydes with dichloro esters or amides and trihalo esters or trichloroamides, respectively. Georg Thieme Verlag Stuttgart.

Asymmetric dehydration of β-hydroxy esters and application to the syntheses of flavane derivatives

Catalytic asymmetric dehydration of β-aryl or alkyl substituted β-hydroxy esters via kinetic resolution has been investigated. A brief survey of 10 different chiral ligands is conducted to examine the effects of chiral ligand structure on selectivity of t

Kinetic resolution of β-alkenyl-, β-alkynyl- and β-flavenyl-substituted β-hydroxy esters in asymmetric dehydration

Catalytic asymmetric dehydration of β-alkenyl- or alkynyl-substituted β-hydroxy esters by kinetic resolution has been investigated with five different chiral ligands 3-7. The kinetic resolution of a variety of racemic β-hydroxy tert-butyl esters in the presence of a prolinol chiral ligand and BrZnCH2CO2tBu provided highly enantio-enriched β-hydroxy esters 9-22 with selectivity factors ranging from 11 to 59. In addition, the application of this asymmetric synthetic methodology to the preparation of enantio-enriched flavene derivatives 23-29 is demonstrated. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.