53354-75-9

Upstream product

• 75-16-1 methylmagnesium bromide 
• 544-97-8 dimethyl zinc(II) 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 917-54-4 methyllithium 
• 5411-56-3 (1S)-1-(2-bromophenyl)ethanol 
• 6630-33-7 ortho-bromobenzaldehyde 
• 403656-49-5 (S)-2-[1-(4-methoxybenzyloxy)ethyl]benzaldehyde 
• 403656-48-4 C₁₆H₁₇BrO₂ 
• 71885-44-4 4,5-dihydro-4,4-dimethyl-2-(2-methylphenyl)-2-oxazoline 
• 679420-02-1 (3R)-3-methyl-1,3-dihydro-2-benzofuran-1-ol 
• 917-64-6 methyl magnesium iodide 
• 215546-09-1 1-{2-[1-(Dimethyl-phenyl-silanyl)-ethyl]-phenyl}-ethanone 
• 215546-10-4 2-[1-(Dimethyl-phenyl-silanyl)-ethyl]-benzaldehyde 
• 215546-07-9 2-{2-[1-(Dimethyl-phenyl-silanyl)-ethyl]-phenyl}-4,4-dimethyl-4,5-dihydro-oxazole 

Downstream Products

• 1012309-76-0 syn 3-[3-(4-methoxybenzyloxy)prop-1-enyl]-1,5-dimethyl-benzo[e]-[1,3]dioxepane 
• 909295-58-5 1-[(S)-1-(isobutyryloxy)ethyl]-2-[(S)-1-hydroxyethyl]benzene 

Relevant academic research and scientific papers

Optical resolution of C2-symmetric racemic 1,4-diols with o-xylylene structure by chiral resolving agent (S)-ALBO-V

Optical resolution of C2-symmetric racemic 1,4-diols, 1,2-bis(1-hydroxyalkyl)benzene, was examined using (S)-5-allyl-2-oxabicyclo[3.3.0]octene ((S)-ALBO-V) as chiral resolving agent. Diastereomeric acetals obtained from the 1,4-diols with (S)-A

NEW CHIRAL DIOLS, THEIR MANUFACTURE AND LIGANDS AND CATALYSTS DERIVED THEREFROM

The present invention relates to a method for the preparation of C2-symmetric 1,4-diols of the formula IVA or IVB, wherein ring A, R1 and R2 have the meanings given in the specification, that makes use of the metallation of pure enantiomers of α-(aryl or heteroaryl)-α-substituted alkanol compounds or the use of said alkanol compounds in the preparation of said mmetric 1,4-diols; novel C2--symmetric 1,4-diols in enantiomerically pure form; and methods of use or their use in the synthesis of chiral ligands which find use to produce catalysts for a variety of asymmetric transformations such as hydrogenations.

Synthesis of α,β-unsaturated dioxanes, dioxolanes and dioxepanes by trans-acetalisation of dimethylacetals with meso or C 2-symmetrical 1,2-, 1,3- and 1,4-diols

Several o-dibenzylic diols were prepared reacting organometallics with o-phthalaldehyde at room temperature in ether. The identity of the meso and C2-symmetrical (D,L) isomers as well as their ratio were determined by chiral gas chromatography. The meso and C2 (racemic) stereoisomeric diols were easily separated by flash chromatography on silica gel. A set of 18 α,β-unsaturated acetals were then prepared reacting those, as well as commercially available 1,2, 1,3 and 1,4 diols, with the corresponding methylacetals in acidic medium. A trans-acetalisation procedure adapted to the cases of fragile allylic alcohols or unfavorable 1,6 diols-derived dioxonanes based on a Dean-Stark trapping of methanol was also employed.

An efficient enantioselective preparation of (S,S)-1,2-bis(1-hydroxyalkyl)benzene

(S,S)-1,2-Bis(1-hydroxyalkyl)benzenes were obtained in >99% ee's with high diastereoselectivity by the enantioselective addition of dialkylzinc to (S)-2-[1-(4-methoxybenzyloxy)alkyl]-benzaldehyde (86% ee) in the presence of a catalytic amount of (S)-2-(4-

Enantioselective dialkylation of 1,2-phthalicdicarboxaldehyde

A new two-step, one-pot procedure is reported for the enantioselective synthesis of C2-symmetric diols derived from 1,2-phthalicdicarboxaldehyde. The first step involves the enantioselective addition of a dialkylzinc compound to one of the aldehyde groups, affording a lactol organozinc derivative. In the second step this lactol derivative is converted to the appropriate diol with the aid of a Grignard reagent and subsequent hydrolysis. This methodology also allows the synthesis of unsymmetric diols.

The stereochemistry of the vinylogous Peterson elimination

Base-induced eliminations of the vinylogous β-hydroxysilanes 7, 9, 11 and 12 are stereospecifically syn, giving largely the trans,trans-diene 8 from 7 and 11, the cis,trans-diene 10 from 9, and the trans,cis-diene 13 from 12. When a cis double bond is produced, it is selectively placed adjacent to the carbon atom that originally carried the hydroxy group. E2′ Reactions with silyl as the electrofugal group and acetate as the nucleofugal group, initiated by fluoride ion, are not stereospecific, but can be highly stereoselective in favour of the trans,trans-diene 8 when the carbon substituent at the silicon-bearing end is a cyclohexyl group and the double bond is cis, and in favour of the trans,cis-diene 13 when the carbon substituent at the silicon-bearing end is a methyl group and the double bond is trans. Attempts to use the Peterson reactions to make o-quinodimethanes stereospecifically failed, with no evidence of 1,4-elimination from the alcohols 40 and 41. The corresponding E2′ reaction from the esters using fluoride ion on the acetates or formates 46 and 47 gave stereoselectively the E,E-quinodimethane 48.