159690-73-0

Upstream product

• 108-24-7 acetic anhydride 
• 159690-72-9 (R)-1-phenyl-2-octanol 
• 81438-46-2 1-iodooct-1-yne 
• 159690-58-1 (R)-7-benzyloxacycloheptan-2-one 

Downstream Products

• 76904-91-1 (R)-3-((R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-nonanoic acid methyl ester 
• 121541-65-9 (R)-(-)-1,3-nonandiol 1 

Relevant academic research and scientific papers

Highly Stereoselective Synthesis and Hydrogenation of (Z)-1-Alkyl-2-arylvinyl Acetates: A Wide Scope Procedure for the Preparation of Chiral Homobenzylic Esters

A synthesis of (Z)-1-alkyl-2-arylvinyl acetates 3 with broad scope is reported by using two complementary methods. The first one uses a stereospecific gold-catalyzed addition of acetic acid to 1-iodo-alkynes, followed by a Suzuki coupling. By the second,

Broad Scope Synthesis of Ester Precursors of Nonfunctionalized Chiral Alcohols Based on the Asymmetric Hydrogenation of α,β-Dialkyl-, α,β-Diaryl-, and α-Alkyl-β-aryl-vinyl Esters

The catalytic asymmetric hydrogenation of trisubstituted enol esters using Rh catalysts bearing chiral phosphine-phosphite ligands (P-OP) has been studied. Substrates covered comprise α,β-dialkyl, α-alkyl-β-aryl, and α,β-diarylvinyl esters, the corresponding hydrogenation products being suitable precursors to prepare synthetically relevant chiral nonfunctionalized alcohols. A comparison of reactivity indicates that it decreases in the order: α,β-dialkyl > α-alkyl-β-aryl > α,β-diaryl. Based on the highly modular structure of P-OP ligands employed, catalyst screening identified highly enantioselective catalysts for α,β-dialkyl (95-99% ee) and nearly all of α-alkyl-β-aryl substrates (92-98% ee), with the exception of α-cyclohexyl-β-phenylvinyl acetate which exhibited a low enantioselectivity (47% ee). Finally, α,β-diarylvinyl substrates showed somewhat lower enantioselectivities (79-92% ee). In addition, some of the catalysts provided a high enantioselectivity in the hydrogenation of E/Z mixtures (ca. Z/E = 75:25) of α,β-dialkylvinyl substrates, while a dramatic decrease on enantioselectivity was observed in the case of α-methyl-β-anisylvinyl acetate (Z/E = 58:42). Complementary deuteration reactions are in accord with a highly enantioselective hydrogenation for both olefin isomers in the case of α,β-dialkylvinyl esters. In contrast, deuteration shows a complex behavior for α-methyl-β-anisylvinyl acetate derived from the participation of the E isomer in the reaction.

Application of Microbial Enantiofacially Selective Hydrolysis in Natural Product Synthesis

Pichia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70percent yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87percent e.e.), to be the starting material for the synthesis of optically active natural products.Methyl (R)-3-hydroxy-12-methyltridecanoate, a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation.Final products were enantiomerically enriched to 94-95percent e.e., by the lipase-mediated enantioselective transesterification, which could remove the minor enantiomer as the corresponding acetate.