127180-75-0

Usage

Type of compound

Alcohol

Substituents

Chloro, phenyl, and propan-1-ol groups

Uses

Synthesis of pharmaceuticals and agrochemicals, chiral building block in asymmetric synthesis

Safety precautions

Toxic chloro group, can cause skin, eye, and respiratory irritation; should be used in well-ventilated areas with appropriate personal protective equipment.

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 19261-37-1 2-chloro-3-phenyl-propionaldehyde 
• 685128-72-7 (S)-2-chloro-hydrocinnamaldehyde 
• 76043-69-1 2,2-dichloro-3-phenylpropionaldehyde 
• 63-91-2 L-phenylalanine 

Downstream Products

• 1311386-65-8 C₁₀H₁₁ClO 
• 685128-72-7 (S)-2-chloro-hydrocinnamaldehyde 
• 127102-53-8 (4R,14R)-4,14-dibenzyl-3,6,9,12,15-pentaoxa-21-azabicyclo<15.3.1>heneicosa-1(21),17,19-triene 
• 127102-59-4 (2R,12R)-1,13-diphenyl-4,7,10-trioxatridecane-2,12-diol 
• 61393-94-0 (R)-2-benzyloxirane 

Relevant academic research and scientific papers

Mechanistically Guided Design of an Efficient and Enantioselective Aminocatalytic α-Chlorination of Aldehydes

The enantioselective aminocatalytic α-chlorination of aldehydes is a challenging reaction because of its tendency to proceed through neutral intermediates in unselective pathways. Herein we report the rational shift to a highly selective reaction pathway involving charged intermediates using hexafluoroisopropanol as solvent. This change in mechanism has enabled us to match and improve upon the yields and enantioselectivities displayed by previous methods while using cheaper aminocatalysts and chlorinating agents, 80-95% less amount of catalyst, convenient temperatures, and shorter reaction times.

Stereodivergent Synthesis of Enantioenriched γ-Butyrolactones Bearing Two Vicinal Stereocenters Enabled by Synergistic Copper and Iridium Catalysis

By virtue of a fundamentally new reaction model of azomethine ylide serving as a two-atom synthon, we present the first example of stereodivergent preparation of γ-butyrolactones via synergistic Cu/Ir-catalyzed asymmetric cascade allylation/lactonization, and all four stereoisomers of γ-butyrolactones bearing two vicinal stereocenters are accessible with excellent diastereoselective and enantioselective control. The chiral IrIII-π-allyl intermediate was separated and characterized to understand the origin of the regio- and stereoselectivity of the initial C?C bond formation process. Control experiments shed some light on the catalyst/substrate and catalyst/catalyst interactions in this dual catalytic system to rationalize the related kinetic/dynamic kinetic resolution process with different catalyst combinations. The enantioenriched γ-butyrolactone products were converted into an array of structurally complex chiral molecules and organocatalysts that were otherwise inaccessible.

A general, enantioselective synthesis of 2-substituted thiomorpholines and thiomorpholine 1,1-dioxides

In the course of our drug discovery programs, we had need to access chiral, 2-substituted thiomorpholines and their oxidized congeners, thiomorpholine 1,1-dioxides. Here, we disclose a high-yielding, general protocol for the enantioselective synthesis of

Mechanistic Studies on the Organocatalytic α-Chlorination of Aldehydes: The Role and Nature of Off-Cycle Intermediates

Herein we report the isolation and characterization of aminal intermediates in the organocatalytic α-chlorination of aldehydes. These species are stable covalent ternary adducts of the substrate, the catalyst and the chlorinating reagent. NMR-assisted kinetic studies and isotopic labeling experiments with the isolated intermediate did not support its involvement in downstream stereoselective processes as proposed by Blackmond. By tuning the reactivity of the chlorinating reagent, we were able to suppress the accumulation of rate-limiting off-cycle intermediates. As a result, an efficient and highly enantioselective catalytic system with a broad functional group tolerance was developed.

Trichloromethanesulfonyl chloride: A chlorinating reagent for aldehydes

Trichloromethanesulfonyl chloride (CCl3SO2Cl), a commercially available reagent, has been found to perform efficiently in the α-chlorination of aldehydes, including its catalytic asymmetric version, under very mild reaction conditions. Under our reaction conditions, this compound outperforms typical chlorinating reagents for organic synthesis, facilitates workup and purification of the product, and minimizes the formation of toxic, chlorinated organic waste.

Organocatalytic asymmetric fluorination of α-chloroaldehydes involving kinetic resolution

In a previous study it was shown that the enantioselective α-fluorination of racemic α-chloroaldehydes with a chiral organocatalyst yielded the corresponding α-chloro-α-fluoroaldehydes with high enantioselectivity. It was also revealed that kinetic resolu

Enantioselective -chlorination of aldehydes with recyclable fluorous (s)-pyrrolidine-thiourea bifunctional organocatalyst

A novel fluorous (S)-pyrrolidine-thiourea bifunctional organocatalyst is prepared. The catalyst shows good activity and enantioselectivity for direct -chlorination of aldehydes using N-chlorosuccinimide (NCS) as the chlorine source. It can be recovered fr

General access to chiral n -alkyl terminal aziridines via organocatalysis

(Figure Presented) A three step, one-pot protocol involving enantioselective α-chlorination of aldehydes, subsequent reductive amination with a primary amine, and SN2 displacement to afford chiral N-alkyl terminal aziridines in 40-65% yield (74-87%/step) and, in most cases, >90% ee is reported.

Enantioselective linchpin catalysis by SOMO catalysis: An approach to the asymmetric a-chlorination of aldehydes and terminal epoxide formation

Time for SOme MOre: For the first time SOMO (singly occupied molecular orbital) activation has been exploited to allow a new approach to the α-chlorination of aldehydes. This transformation can be readily implemented as part of a linchpin catalysis approach to the enantioselective production of terminal epoxides.

Enantioselective protonation of catalytically generated chiral enolates as an approach to the synthesis of α-chloroesters

Treatment of α,α-dichloroaldehydes with various phenols in the presence of chiral triazolium salt catalysts and excess base results in the synthesis of α-chloro aryl esters in good yield and enantioselectivity. The reaction is tolerant of various function