141339-56-2

Upstream product

• 532-32-1 sodium benzoate 
• 19265-24-8 1-chloropentane-2-one 
• 634196-62-6 4,4,5,5-tetramethyl-2-(pent-1-yn-1-yl)-1,3,2-dioxaborolane 
• 141339-91-5 t-butyl 2-chloro-3-oxohexanoate 
• 61540-30-5 3-oxohexanoic acid tert-butyl ester 

Downstream Products

• 141339-73-3 Benzoic acid (R)-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-pentyl ester 
• 141339-73-3 Benzoic acid (S)-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-pentyl ester 

Relevant academic research and scientific papers

Access to Vinyl Ethers and Ketones with Hypervalent Iodine Reagents as Oxy-Allyl Cation Synthetic Equivalents

We report an Umpolung strategy of enol ethers to generate oxy-allyl cation equivalents based on the use of hypervalent iodine reagents. Under mild basic conditions, the addition of nucleophiles to aryloxy-substituted vinylbenziodoxolone (VBX) reagents, easily available in two steps from silyl alkynes, resulted in the stereoselective formation of substituted aryl enol ethers. The reaction was most efficient with phenols as nucleophiles, but preliminary results were also achieved for C- and N- nucleophiles. In absence of external nucleophiles, the 2-iodobenzoate group of the reagent was transferred. The obtained aryl enol ethers could then be transformed into α-difunctionalized ketones by oxidation. The described “allyl cation”-like reactivity contrast with the well-established “vinyl-cation” behavior of alkenyl iodonium salts.

A Systematic Study on the Bakers'Yeast Reduction of 2-Oxoalkyl Benzoates and 1-Chloro-2-alkanones

The bakers' yeast reduction of a series of 2-oxoalkyl arenecarboxylates (1a-f) (R=CH3 to n-C6H13; X=H) and the phenyl-modified derivatives (1g-l) (R=n-C5H11, X=OH, CH3, F, Cl, Br, or I) as well as 1-chloro-2-alkanones R(C=O)CH2Cl (6a-f) (R=CH3 to n-C6H13) were systematically investigated.The substrate specificities, configuration and percentee of the reduction products were found to be highly dependent on the length of the alkyl group (R) and the α substituent.Thus, the benzoates 1a-f gave optically active 2-hydroxyalkyl benzoates (2a-f) (R, configuration, percentee) (a: CH3, S, 99; b: C2H5, S, 98; c: C3H7, S, 26; d: n-C4H9, R, 55; e: n-C5H11, S, 15; f: n-C6H13, S, 63) in 11-91percent yields.Among the modification experiments of the phenyl group, 1g-l, the p-iodo substituent markedly increased the ee from 15 to 71percent, although the yield was rather lowered (22percent yield).The reduction of α-chloro ketones 6a-f also gave optically active 1-chloro-2-alkanols (7a-f) in 16-69percent yields.