209530-22-3

Upstream product

• 100929-33-7 (R)-2-amino-2-(4-methoxyphenyl)-1-ethanol 
• 91-13-4 α,α'-dibromo-o-xylene 
• 159848-74-5 1,1-dimethylethyl (R)-N-[2-hydroxy-1-(4-methoxyphenyl)-ethyl]carbamate 
• 637-69-4 4-Methoxystyrene 

Relevant academic research and scientific papers

Asymmetric aminohydroxylation of substituted styrenes: Applications in the synthesis of enantiomerically enriched arylglycinols and a diamine

The catalytic asymmetric aminohydroxylation of a variety of styrene derivatives and vinyl aromatics using osmium tetroxide in conjunction with alkaloid-derived ligands [e.g. (DHQ)2PHAL or (DHQD)2-PHAL] and haloamine salts of alkyl carbamates (e.g. ethyl carbamate or tert-butyl carbamate) has been investigated. By observing the effect of different aromatic substituents and alkyl carbamates on the regioselectivity, yield and enantioselectivity of the aminohydroxylation reactions, a number of conclusions have been reached: (i) the 1-aryl-2-hydroxyethylamine regioisomers were obtained as the major products in reasonable yield and high (≤87%) enantiomeric excess; (ii) tert-butyl carbamate was superior to ethyl carbamate in terms of yield, enantioselectivity and ease of removal of the N-protecting group; (iii) high (≥96%) enantioselectivity was observed with a 4-methoxy-substituted styrene whereas ortho-substituted styrenes gave lower enantioselectivities; (iv) chiral ligands (DHQ)2PHAL and (DHQD)2PHAL gave essentially equal and opposite senses and degrees of asymmetric induction; (v) regioselectivity was ligand dependent with better regioselectivity (and therefore higher isolated yields) obtained with (DHQ)2PHAL than with (DHQD)2PHAL. The products of the aminohydroxylation reactions were used to prepare enantiomerically enriched arylglycinols and a chiral diamine.

Asymmetric aminohydroxylation of substituted styrenes using t-butyl carbamate

A variety of substituted styrenes have been aminohydroxylated using t- butyl carbamate to give either enantiomer of highly enantiomerically enriched N-Boc protected amino alcohols in good yields. Better levels of regioselectivity were observed with (DHQ)2PHAL than with (DHQD)2PH. AL even though the enantioselectivities observed were comparable. One of the amino alcohol products was converted into a novel chiral diamine.