65451-95-8

Upstream product

• 124095-80-3 (E)-(R*,S*)-5-chloro-3-hexen-2-yl acetate 
• 124095-79-0 (E)-(R*,R*)-5-chloro-3-hexen-2-yl acetate 
• 26549-24-6 (2R)-hexan-2-ol 
• 201230-82-2 carbon monoxide 
• 103367-31-3 methyl (S)-5,6-dihydroxy-2(R,S)-methylhexanoate 
• 97204-42-7 (+/-)-(2S*,6R*)-2,6-dimethyldihydropyr-4-en-2-one 
• 62717-99-1 2-methyl-1,5-hexanediol 
• 103367-35-7 methyl 2(R,S)-methyl-5(S)-(tetrahydropyranyloxy)-6-<(tolylsulfonyl)oxy>hexanoate 
• 103367-33-5 methyl 5(S)-hydroxy-2(R,S)-methyl-6-<(tolylsulfonyl)oxy>hexanoate 
• 103367-29-9 methyl (S)-5,6-(isopropylidenedioxy)-2-(R,S)-methylhexanoate 
• 103367-37-9 methyl 2(R,S)-methyl-5(R)-(tetrahydropyranyloxy)-hexanoate 
• 18397-48-3 3,6-dimethyltetrahydro-2H-pyran-2-ol 
• 45741-23-9 4-Hydroxy-3,6-dimethyl-tetrahydro-pyran-2-one 
• 74259-32-8 5,6-dihydro-3,6-dimethyl-4-hydroxy-2H-pyran-2-one 

Relevant academic research and scientific papers

STEREOCONTROLLED SYNTHESIS OF (R*R*)- AND (R*S*)-5-HYDROXY-2-METHYLHEXANOIC ACID LACTONES. PHEROMONE OF THE CARPENTER BEE VIA PALLADIUM-CATALYZED REACTIONS

(E,Z)-2,4-Hexadiene was transformed to the lactone cis-1(>93percent cis)(pheromone of the carpenter bee) in a stereospecific reaction sequence via a Pd-catalyzed 1,4-acetoxychlorination.The same reaction sequence applied to (E,E)-2,4-hexadiene afforded th

Remote control of regio- and diastereoselectivity in the hydroformylation of bishomoallylic alcohols with catalytic amounts of a reversibly bound directing group

(Figure Presented) Remote and reversible! Phosphinites serve as reversibly bound directing groups for the remote control of the regio- and diastereoselective hydroformylation of bishomoallylic alcohols (see scheme; r.r: regioisomer ratio). The distance between the double bond and the functional hydroxy group to which the directing group is reversibly bound is the longest ever reported.

An easy and versatile approach to the synthesis of chiral pheromone lactones via 4,4-dimethyl-2-oxazoline derivatives

As part of our ongoing investigation on the versatility of 4,4-dimethyl-2-oxazoline derivatives, we present a straightforward synthesis of chiral lactone pheromones from readily available starting materials. As an application, we describe the diastereoselective synthesis of cis and trans-2-methyl-5-hexanolide (1), a pheromone component of the carpenter bee Xylocopa hirutissima, and a formal synthesis of (4R,5Z)-5-tetradecen-4-olide (2), the sex pheromone of the Japanese beetle Popillia japonica.

New strategies in carbonylation chemistry: The synthesis of δ-lactones from saturated alcohols and CO

This paper describes the δ-carbonylation of saturated alcohols which uses a 1,5-hydrogen-transfer reaction of alkoxyl radicals and subsequent carbonylation at the δ-carbon atoms as the key. The carbonylation reactions of five classes of saturated alcohols, namely, primary alcohols having primary δ-carbons, primary alcohols having secondary δ-carbons, primary alcohols having tertiary δ-carbons, secondary alcohols having primary δ- carbons, secondary alcohols having secondary δ-carbons, were carded out, in which lead tetraacetate (LTA) was used as a one-electron oxidant to generate the alkoxyl radicals. Carbonylation of these saturated alcohols, except for primary alcohols having tertiary δ-carbons, took place to afford δ-lactones in moderate to good yields. The mechanism of the remote carbonylation likely involves (1) alkoxyl radical generation via LTA oxidation of a saturated alcohol, (2) conversion of this alkoxyl radical to a δ-hydroxyalkyl radical by a 1,5-hydrogen-transfer reaction, (3) CO trapping of the δ-hydroxyalkyl radical yielding an acyl radical, and (4) oxidation and cyclization of the acyl radical to give a δ-lactone. A metal salt-free system was also tested for a substrate derived from a tertiary alcohol having a secondary δ- carbon; the photolysis of an alkyl 4-nitrobenzenesulfenate under CO pressures gave a δ-lactone in moderate yield.

Remote Stereocontrol by utilizing Intramolecular Carbonyl Reduction with Boranes

A simple and efficient method for the remote (1,4- and/or 1,5-) stereocontrol was realized by utilizing an intramolecular carbonyl reduction with ThexBH2 (Thex = 1,1,2-trimethylpropyl).

EPOXY-SILANES IN ORGANIC SYNTHESIS

Stereoselective reactions involving functionalised β,γ-epoxysilanes and epoxide-allylsilanes provide a range of synthetically useful transformations.

Selective 1,4-Chiral Induction in the Reaction of Enolates Generated from t-Butyl δ-Hydroxy Carboxylates

Lithium enolates generated from t-butyl esters of δ-hydroxy carboxylic acids with lithium dialkylamides in THF-HMPA were alkylated stereoselectively to give the corresponding syn-α-alkylated δ-hydroxy esters.The generation of the enolates was accelerated by the addition of lithium trifluoromethanesulfonate, and the successive aldol and hydroxylation reactions of the enolates also proceeded in a stereoselective manner.

NATURAL PRODUCT SYNTHESIS USING ?-ALLYLTRICARBONYLIRON LACTONE COMPLEXES: SYNTHESIS OF PARASORBIC ACID, THE CARPENTER BEE PHEROMONE AND MALYNGOLIDE

Preparation of three δ-lactonic natural products, parasorbic acid, the carpenter bee pheromone and malyngolide has been achieved from ?-allyltricarbonyliron lactone complexes as the key synthesis intermediates.