6118-13-4

Upstream product

• 598-32-3 2-hydroxy-3-butene 
• 844641-16-3 (S)-threonyl-(S)-phenylglycine 
• 42969-65-3 (R)-(+)-3-butyn-2-ol 
• 65001-62-9 3-buten-2-yl benzoate 
• 925669-95-0 2,3-cis-epoxybutane 
• 78-94-4 methyl vinyl ketone 

Downstream Products

• 4221-99-2 (S)-2-butanol 
• 130404-07-8 (R)-3-chloro-but-1-ene 
• 121523-85-1 (αS)-erythro-α-methyl-3-phenyl-2-isoxazoline-5-methanol 
• 121523-84-0 (αS)-threo-α-methyl-3-phenyl-2-isoxazoline-5-methanol 
• 90270-43-2 benzoic acid (S)-1-methylallyl ester 
• 143264-39-5 tert-butyl{[(1S)-1-methyl-2-propenyl]oxy}diphenylsilane 
• 1208377-51-8 C₁₄H₁₅F₃O₃ 
• 888504-79-8 (1R)-1-methylprop-2-enyl (4S)-4-(benzyloxy)-5,5-dimethoxy pentanoate 
• 479213-74-6 1,3,5-tribromo-2-(allyloxymethyl)-4,6-bis((1S)'-methyl-2'-propenyloxymethyl)-benzene 

Relevant academic research and scientific papers

Are Highly Stable Covalent Organic Frameworks the Key to Universal Chiral Stationary Phases for Liquid and Gas Chromatographic Separations?

High-performance liquid chromatography (HPLC) and gas chromatography (GC) over chiral stationary phases (CSPs) represent the most popular and highly applicable technology in the field of chiral separation, but there are currently no CSPs that can be used for both liquid and gas chromatography simultaneously. We demonstrate here that two olefin-linked covalent organic frameworks (COFs) featuring chiral crown ether groups can be general CSPs for extensive separation not only in GC but also in normal-phase and reversed-phase HPLC. Both COFs have the same 2D layered porous structure but channels of different sizes and display high stability under different chemical environments including water, organic solvents, acids, and bases. Chiral crown ethers are periodically aligned within the COF channels, allowing for enantioselective recognition of guest molecules through intermolecular interactions. The COF-packed HPLC and GC columns show excellent complementarity and each affords high resolution, selectivity, and durability for the separation of a wide range of racemic compounds, including amino acids, esters, lactones, amides, alcohols, aldehydes, ketones, and drugs. The resolution performances are comparable to and the versatility is superior to those of the most widely used commercial chiral columns, showing promises for practical applications. This work thus advances COFs with high stability as potential universal CSPs for chromatography that are otherwise hard or impossible to produce.

Inclusion of aliphatic alcohols in pockets of (S)-threonyl-(S)- phenylglycine using grinding method

Inclusion compounds of a dipeptide, (S)-threonyl-(S)-phenylglycine (Thr-Phg), with several aliphatic alcohols were easily prepared by grinding them in a mortar. Thr-Phg molecules arranged in antiparallel to construct a sheet, and guest alcohols were accommodated in a chiral pocket between the sheets. 3-Butyn-2-ol and 2-butanol were included with moderate enantioselectivity, 57% ee (R) and 49% ee (R), respectively. The role of the hydroxy group of Thr-Phg is not only to construct the unique pocket but also to capture guest alcohols by hydrogen bonding.

H-bonding as a control element in stereoselective Ru-catalyzed olefin metathesis

(Chemical Equation Presented) H-bonding interactions have been exploitedextensively in the design of catalysts for stereoselective synthesis bu t have rarely been utilized in the development of metal-catalyzed processes. Studies described herein demonstrate that intramolecular H-bonding interactions can significantly increase the rate and levels of stereochemical control in Ru-catalyzed olefin metathesis reactions. The utility of H-bonding in catalytic olefin metathesis is elucidated through development of exceptionally facile and highly diastereoselective ring-opening/cross-metathesis (DROCM) reactions, involving achiral Ru catalysts and enantiomerically enriched allylic alcohols. Transformations proceed to completion readily (>98percent conversion, up to 87percent yield), often within minutes, in the presence of ≤2 mol percent of an achiral catalyst to afford synthetically versatile products of high stereochemical purity (up to >98:2 dr and 11:1 E:Z).

The effect of catechin derivatives on the enantioselectivity of lipase-catalyzed hydrolyses of alkynol benzoate esters

Polyphenols, such as (+)-catechin and pyrogallol could be used to enhance stereochemical control in the lipase-catalyzed hydrolysis of alkynol benzoate esters, leading to increased enantioselectivities in the kinetic resolution of alkynols with lipase Amano AH.

An Asymmetric Transformation of Symmetrical Epoxides to Both Enantimers of Allylic Alcohols by Chiral Lithium Amides

Both enantiomers of several optically active allylic alcohols are obtained from cyclic and acyclic symmetrical epoxides by using chiral lithium amides, i.e., lithium cyclohexylmethylamide or lithium (S)-2-pyrrolidide, as bases.

Selective Reductions. 37. Asymmetric Reduction of Prochiral Ketones with B-(3-Pinanyl)-9-borabicyclononane

The chiral trialkylborane B-(3-pinanyl)-9-borabicyclononane, either with the neat reagents or concentrated solutions, 2 M, reduces a wide range of prochiral carbonyl compounds with good to excellent asymmetric induction.Reduction of simple dialkyl ketones, 2-butanone, 2-octanone, 3-methyl-2-butanone, and 3,3-dimethyl-2-butanone, yields the corresponding alcohols with 43percent, 48percent, 62percent, and 0.7percent asymmetric induction.Acetophenone is reduced to 1-phenylethanol in 85percent ee.The α,β-unsaturated ketones 3-buten-2-one, 1-acetyl-1-cyclohexene, 3-methyl-2-cyclohexenone, and trans-4-phenyl-3-buten-2-one are reduced to the corresponding allylic alcohols with 57percent, 64percent, 11percent, and 97percent asymmetric induction, respecticvely.The α,β-conjugated acetylenic ketones 3-butyn-2-one, 4-methyl-1-pentyn-3-one, and 4-phenyl-3-butyn-2-one underwent a rapid reduction to afford the corresponding propargylic alcohols with 79percent, 99percent, and 91percent enantiomeric purities.The α-haloalkyl aromatic ketones α-chloroacetophenone, α-bromoacetophenone, α-iodoacetophenone, α,p-dibromoacetophenone, α-bromo-p-cyanoacetophenone,α-bromo-2'-acetonaphthone,and α,α,α-trifluoroacetophenone afforded the corresponding halohydrins with 96percent,93percent,93percent,96percent,96percent,90percent,and35percent enantiomeric purities, respectively.The corresponding aliphatic analogue 1-bromo-3-methyl-butanone gave the halohydrin in 66percent ee.The other isomer of this ketone, 3-bromo-3-methyl-2-butanone, failed to undergo reduction.Both the aliphatic and aromatic α-keto esters underwent rapid reduction to give the corresponding α-hydroxy esters with excellentenantiomeric excesses.Thus, methyl, ethyl, isopropyl, and tert-butyl pyruvates afforded the corresponding lactates with 86percent,83percent,78percent, and 92percent ee at 25 deg C,respectively.Lowering the reaction temperature to 0 deg C gave the tert-butyl lactate in 100percent ee.Other aliphatic α-keto esters such as metyl and ethyl 2-oxopentanoates, methyl 3-methyl-2-oxobutanoate, and ethyl 4-methyl-2-oxopentanoate were reduced to the corresponding α-hydroxy esters with 96percent, 96percent, 11percent, and 82percent ee.The methyl, isopropyl, and tert-butyl benzoylformates were reduced to the corresponding mendelic esters with 90percent, 96percent and 100percent ee, respectively.The reduction of the β-keto esters, however, proceeded slowly and ethyl acetoacetate gave the corresponding alcohol with 55percent ee.