139164-92-4

Upstream product

• 4798-44-1 1-hexene-3-ol 
• 928-94-9 (Z)-2-hexen-1-ol 
• 14861-06-4 vinyl 2-butenoate 
• 142204-60-2 (2S,3R)-3-benzoyloxy-1,2-hexanediol 
• 89321-71-1 (2S,3S)-3-propyl-2-oxiranemethanol 
• 149494-24-6 [(2R,3R)-3-propoxiran-2-yl]methyl p-toluenesulfonate 
• 106498-75-3 2,3-epoxyhexanol 
• 149396-64-5 (2S,3R)-2-(bromomethyl)-3-propyloxirane 
• 142204-61-3 (-)-(R)-hex-1-en-3-yl benzoate 

Downstream Products

• 108340-61-0 (R)-1,2-pentanediol 
• 92418-71-8 (2R,3R)-2,3-epoxy-1-hexanol 
• 142236-55-3 (2R,3R)-1,2-epoxy-3-hexanol 
• 53101-38-5 3-chloro-1-hexene 
• 139079-86-0 (3R)-hex-1-en-3-yl (R)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetate 
• 142204-61-3 (-)-(R)-hex-1-en-3-yl benzoate 
• 152212-36-7 (R)-3-Hydroxy-2-hexanone 

Relevant academic research and scientific papers

Rhodium-Catalyzed Dynamic Kinetic Asymmetric Allylation of Phenols and 2-Hydroxypyridines

Inspired by the mechanistic studies of rhodium-catalyzed atom-economic addition of carboxylate acids to allenes, a rhodium-catalyzed dynamic kinetic asymmetric allylation of different nucleophiles with racemic allylic carbonates has been developed. High regio- and enantioselectivities can be obtained under neutral conditions and, furthermore, the chemoselectivities can be controlled by different diphosphine ligands. (R,R)-QuinoxP* leads to selective O-allylation of phenols, whereas when embedding (S,S)-DIOP as the ligand, 2-naphthol is ortho-C-allylated for the first time in high enantioselectivity. To this end, hydroxypyridines can be N-allylated by RhI/(S)-DTBM-Segphos via the same intermediate as in the previously reported atom-economic addition to allenes.

Chemoenzymatic synthesis of optically active γ-alkyl-γ-butenolides

rac-Hept-1-en-3-ol 4 was subjected to an enantioselective esterification in the presence of Novozyme 435 and vinyl crotonate as the acyl donor to give (3S)-oct-1-en-3-yl crotonate 7 in >99% ee and (3R)-alcohol 4 in 99% ee. The E-value of this enzymatic reaction was found to be >1000. The (S)-crotonic ester 7 was converted by ring-closing metathesis (RCM) using Grubbs' catalyst to give (S)-oct-2-en-4-olide 1 in 96% yield while keeping the high enantiomeric excess.

Synthesis of (3R)-3-Hydroxy-2-hexanone, (2R,3R)-2,3-Hexanediol and (2S,3R)-2,3-Hexanediol, the Male Sex Pheromone of Hylotrupes bajulus and Pyrrhidium sanguineum (Cerambycidae)

The following compounds were identified as male pheromone components of the longhorn beetles Hylotrupes bajulus and Pyrrhidium sanguineum: (3R)-3-hydroxy-2-hexanone , (2S,3R)-2,3-hexanediol and (2R,3R)-2,3-hexanediol .The syntheses of enantiomerically pure samples, enantiomeric separation by chiral gas chromatography and unambiguous structure assignment of the target compounds are described. - Key Words: Cerambycidae / Longhorn beetle / Pheromones / Ketones, α-hydroxy- / Hylotrupes bajulus / Pyrrhidium sanguineum

Larger Scale Preparation of Optically-active Allylic Alcohols

An efficient and practical synthesis of optically-active allylic alcohols from 2,3-epoxytoluene-p-sulfonates by the in situ formation of the epoxy iodides and their subsequent reduction with zinc-copper couple has been established.Application of this procedure to the larger-scale synthesis of (S)-(+)-but-3-en-2-ol from (2S,3S)-3-methylglycidyl toluene-p-sulfonate has also been investigated.

A New Approach to the Synthesis of Chiral Vinyl Carbinols from 2,3-Epoxy Alcohols

The regioselective opening with benzoic acid of 2,3-epoxy alcohols obtained from the asymmetric epoxidation of 2,3-allylic alcohols, and deoxygenation of the resulting diol benzoates provides an effective, general and simple method to convert chiral 2,3-epoxy alcohols, into vinyl carbinols without the loss of any optical purity.