14366-91-7

Upstream product

• 25201-44-9 (1S,2S)-2-methyl-1-phenyl-3-buten-1-ol 
• 17226-81-2 ethyl (2R*,3S*)-3-hydroxy-2-methyl-3-phenylpropanoate 
• 205692-08-6 (2R,3S)-3-Hydroxy-2-methyl-3-phenyl-propionic acid (1R,2S)-2-[methyl-(1,2,3,4,5,6,7,8-octahydro-anthracene-9-sulfonyl)-amino]-1-phenyl-propyl ester 
• 100-52-7 benzaldehyde 
• 123-38-6 propionaldehyde 
• 74-85-1 ethene 
• 16735-22-1 (S)-3-hydroxy-2-methyl-1-phenylpropan-1-one 
• 1631-83-0 diphenylsilyl chloride 
• 32742-19-1 methyl 2-benzoylpropionate 
• 53403-04-6 (+)-(1S,2S)-1-methyl-2-phenylcyclopropane 
• 637-50-3 1-phenylpropene 
• 138702-88-2 (4R,5R)-1,3-Bis-((2R,3R)-3-hydroxy-2-methyl-3-phenyl-propionyl)-4,5-diphenyl-imidazolidin-2-one 
• 157197-94-9 (4S,5S)-1,3-di(3-phenyl-3-hydroxy-2-methylpropionyl)-4,5-di(methoxymethyl)imidazolidin-2-one 
• 157197-98-3 (4S,5S)-1,3-di(3-phenyl-3-hydroxy-2-methylpropionyl)-4,5-di(benzyloxymethyl)imidazolidin-2-one 

Downstream Products

• 22821-07-4 2-(butylthio)benzo[d]oxazole 
• 2382-96-9 2-sulfanyl-1,3-benzoxazole 
• 84784-81-6 erythro-2-methyl-3-phenyl-1,3-propanediol 1-methoxyethoxymethyl ether 

Relevant academic research and scientific papers

Confinement-Controlled, Eithersyn- oranti-Selective Catalytic Asymmetric Mukaiyama Aldolizations of Propionaldehyde Enolsilanes

Protected aldols (i.e., true aldols derived from aldehydes) with eithersyn- oranti- stereochemistry are versatile intermediates in many oligopropionate syntheses. Traditional stereoselective approaches to such aldols typically require several nonstrategic

Copper-Catalyzed Stereospecific Hydroboration of Internal Allylic Alcohols

An effective Cu-catalyzed stereospecific hydroboration of aliphatic and aromatic 1,1,2-trisubstituted internal allylic alcohols has been reported. This reaction proceeds via a silyl ether transient protection of allylic alcohols and subsequent stereospecific hydroboration. Followed by an oxidative workup, an array of acyclic, cyclic, and heterocyclic 1,3-diols was synthesized in good to excellent yields with good functional group tolerance and excellent diastereomeric ratios (> 20:1).

Synthesis of Ynolates via Double Deprotonation of Nonbrominated Esters

Herein, we report a double deprotonation method used for the preparation of ynolates starting from nonbrominated 2,6-di-tert-butylphenyl esters. The current method is superior to the previously described double lithium/halogen exchange approach because easily accessible starting materials are used. This method will be especially useful for preparation of ynolates bearing functional groups in organic synthesis.

Lewis Base-Promoted Ring-Opening 1,3-Dioxygenation of Unactivated Cyclopropanes Using a Hypervalent Iodine Reagent

A facile and effective system has been developed for the regio- and chemoselective ring-opening/electrophilic functionalization of cyclopropanes through C?C bond activation by [bis(trifluoroacetoxy)iodo]benzene with the aid of the Lewis basic promoter p-toluenesulfonamide. The p-toluenesulfonamide-promoted system works well for a wide range of cyclopropanes, resulting in the formation of 1,3-diol products in good yields and regioselectivity.

Direct Catalytic Asymmetric Aldol Reaction of α-Alkylamides

A catalytic asymmetric aldol reaction directly employing amides as latent enolates has remained elusive because of the resistance of amides to enolization. A direct aldol reaction of α-alkylamides without any electron-withdrawing group harnessed by specif

SN2 Reactions at Tertiary Carbon Centers in Epoxides

Described herein is a novel concept for SN2 reactions at tertiary carbon centers in epoxides without activation of the leaving group. Quantum chemical calculations show why SN2 reactions at tertiary carbon centers are proceeding in these systems. The reaction allows flexible synthesis of 1,3-diol building blocks for natural product synthesis with excellent control of the relative and absolute configurations.

Sterically Hindered Chiral Ferrocenyl P,N,N-Ligands for Highly Diastereo-/Enantioselective Ir-Catalyzed Hydrogenation of α-Alkyl-β-ketoesters via Dynamic Kinetic Resolution

A new class of sterically hindered chiral ferrocenyl P,N,N-ligands have been prepared through a two-step transformation from (Sc,Rp)-PPFNH2, in which a new (R)-stereogenic center at the pyridinylmethyl position was generated in high diastereoselectivity. With these newly developed P,N,N-ligands, Ir-catalyzed asymmetric hydrogenation of various α-alkyl-substituted β-aryl-β-ketoesters via dynamic kinetic resolution has been realized in high diastereo- and enantioselectivities for the first time, which led to a variety of optically active anti-β-hydroxyesters in up to 99% ee. The study indicated that the additional stereocenter at the pyridinylmethyl position of these ligands is crucial to realize this hydrogenation.

Catalytic Asymmetric Iterative/Domino Aldehyde Cross-Aldol Reactions for the Rapid and Flexible Synthesis of 1,3-Polyols

We report here catalytic asymmetric iterative and domino cross-aldol reactions between aldehydes, endowed with a high level of robustness, flexibility, and generality. A Cu(I)-DTBM-SEGPHOS complex catalyzes an asymmetric cross-aldol reaction between acceptor aldehydes and boron enolates derived from donor aldehydes, which are generated through Ir-catalyzed isomerization of allyloxyboronates. The unit process can be repeated using the aldol products in turn as acceptor substrates for the subsequent asymmetric aldol reaction. The donor aldehydes and stereoselectivity can be flexibly switched in a stepwise manner for the double-aldol reaction. Furthermore, asymmetric triple- and quadruple-aldol reactions are possible in one-pot using the appropriate amounts of donors and amine additives, rapidly elongating the carbon skeleton with controlling up to eight stereocenters. The method should be useful for straightforward synthesis of enantiomerically and diastereomerically enriched 1,3-polyols.

Highly diastereoselective hydrosilylations of allylic alcohols

The highly syn-selective hydrosilylation of allylic alcohols was developed which, following oxidation, provided 1,3 alcohols containing two contiguous stereocentres. Through judicious choice of silane the complementary anti-selective hydrosilylation was a

Highly diastereo- and enantioselective allylboration of aldehydes using α-substituted allyl/crotyl pinacol boronic esters via in situ generated borinic esters

Readily available, α-substituted allyl/crotyl pinacol boronic esters often give low E/Z selectivity (with Z favored) in reactions with aldehydes. We found that addition of nBuLi to the pinacol boronic ester followed by trapping of the alkoxide with TFAA leads to an intermediate allyl borinic ester which undergoes allylboration with very high E selectivity. The substrate scope includes primary to tertiary alkyl α-substituents, crotyl substrates, and the previously unreported β-methallyl pinacol boronic esters. The latter give very high Z selectivity under standard conditions which is completely reversed to high E selectivity under the new conditions. Monitoring the reaction by 11B NMR confirmed that the reaction proceeds through a borinic ester intermediate.