1004-58-6

Usage

Synthesis Reference(s)

Tetrahedron, 48, p. 1449, 1992 DOI: 10.1016/S0040-4020(01)92233-1

Upstream product

• 6954-16-1 (R,S)-6-chloro-1,4-dioxaspiro<4.5>decane 
• 1728-15-0 (R,S)-6-bromo-1,4-dioxaspiro<4.5>decane 
• 75-21-8 oxirane 
• 930-68-7 cyclohexenone 
• 107-21-1 ethylene glycol 
• 108-94-1 cyclohexanone 
• 822-87-7 2-Chlorocyclohexanone 
• 110-83-8 cyclohexene 
• 7381-30-8 2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane 

Downstream Products

• 930-68-7 cyclohexenone 
• 15353-17-0 3-Trinitromethyl-cyclohexanon 
• 72757-56-3 1-β-Hydroxyethoxy-3-butyl-cyclohexen 
• 88116-46-5 1-butyl-2-cyclohexen-1-ol 
• 128913-72-4 trans-7-fluoro-6-(phenylseleno)-1,4-dioxaspiro<4,5>decane 
• 69035-58-1 1-(tert-butyl)cyclohex-2-en-1-ol 
• 91043-58-2 2-(3-tert-Butyl-cyclohex-1-enyloxy)-ethanol 
• 73223-83-3 1,4-dioxaspiro[4,5]decan-9-ol 
• 4096-34-8 cyclohex-3-enone 
• 19770-37-7 6,7-epoxy-1,4-dioxaspiro<4,5>decane 
• 19770-37-7 3,3-ethylenedioxycyclohehene oxide 
• 19770-37-7 C₈H₁₂O₃ 
• 591-24-2 3-Methylcyclohexanone 
• 7092-24-2 1,4-dioxaspiro<4.5>dec-7-ene 

Relevant academic research and scientific papers

Facile Procedure for Acetalization Using Diols, Alkoxysilane and a Catalytic Amount of Trimethylsilyl Trifluoromethanesulfonate

In the presence of sec- or tert-alkoxysilane and a catalytic amount of trimethylsilyl trifluoromethanesulfonate (TMSOTf), carbonyl compounds react with various diols to give acetals in high yields.

A FACILE PROCEDURE FOR ACETALIZATION UNDER APROTIC CONDITIONS

Carbonyl compounds are readily acetalized by alkoxysilanes in the presence of trimethylsilyl trifluoromethanesulfonate catalyst.

Cadmium iodide catalyzed and efficient synthesis of acetals under microwave irradiations

A new selective method of acetalization of aldehydes and ketones with 1,2-diols, 1,3-diols or alcohols mediated by cadmium iodide under microwave irradiation is achieved in excellent yields.

Distannoxane-catalyzed acetilization of carbonyls

1,3-Disubstituted tetrabutyldistannoxanes catalyze acetilization of carbonyl compounds under mild conditions. Thorough investigations of factors influencing this reaction are given. A variety of synthetically useful carbonyl compounds are efficiently converted to acetals. In particular, acetilization of cyclic α,β-unsaturated ketones is readily achieved which have met with only limited success so far.

Polyaniline-Supported Sulfuric Acid Salt as a Powerful Catalyst for the Protection and Deprotection of Carbonyl Compounds

Structurally different carbonyl compounds were converted into their corresponding cyclic acetals using polyaniline-sulfate salt as catalyst in dry toluene in excellent yield. In turn, useful deacetalization in aqueous medium was demonstrated. Chemoselective protection of carbonyl compounds was also demonstrated. The advantages of the polyaniline-sulfate salt are ease of preparation and handling, stability, reusability and activity.

An Enantioselective Approach to 4-O-Protected-2-cyclopentene-l,4-diol Derivatives via a Rhodium-Catalyzed Redox-Isomerization Reaction

Kinetic resolution of a series of cyclopentene-1,4-diol derivatives has been successfully achieved with enantiomeric excess up to 99.4% and a kf/ks ratio of 55 by a rhodium-catalyzed redox-isomerization reaction in a noncoordinating solvent.

Auxiliary controlled singlet-oxygen ene reactions of cyclohexenes

The photooxygenation of homochiral cyclohexene ketals, which are easily available from 2-cyclohexenone and l-tartrates, affords hydroperoxides and after reduction the corresponding allylic alcohols in good yields and high regioselectivities. This can be rationalized by electronic repulsions in a perepoxide intermediate and provides evidence for unfavorable 1,3 diaxial interactions with a dioxolane oxygen atom. Only low stereoselectivities were observed, due to the flexibility of the cyclohexene ring. However, the diastereomers could be separated and after cleavage of the auxiliary, 4-hydroxy-2-cyclohexen-1-one was isolated in enantiomerically pure form, which can serve as a building block for natural product synthesis.

Intramolecular chromium(II)-catalyzed pinacol cross coupling of 2-methylene-α,ω-dicarbonyls

Using only 10% of CrCl2 as catalyst, manganese-powder as reducing agent and TMSC1 as scavenger, 2-methylene-α,ω-dialdehydes and -ketones can be coupled to form cyclic diols diastereoselectively. The diastereomeric excess strongly depends on the ring size and the substituents of the ω-carbonyl group. The greater the ring size the higher diastereoselectivities are observed. In all cases cis-diols are preferentially formed.

Convenient preparation of cyclic acetals, using diols, TMS-source, and a catalytic amount of TMSOTf

With use of diol, alkoxysilane, and a catalytic amount of trimethylsilyl trifluoromethanesulfonate (TMSOTf), carbonyl compounds are converted to acetals in good yields under mild conditions. This procedure, which was carried out without synthesizing the silylated diols, is a more convenient adaptation of Noyori's method. This acetalization applies to not only simple but also conjugated carbonyl compounds. Moreover, various TMS compounds, including solid supported compounds, are effective for this method instead of alkoxylsilane.

Catalytic asymmetric epoxidation

A compound and method for producing an enantiomerically enriched epoxide from an olefin using a chiral ketone and an oxidizing agent is disclosed.