177770-85-3

Upstream product

• 67-56-1 methanol 
• 55339-40-7 (3-oxo-cyclohexyl)-acetaldehyde 
• 930-68-7 cyclohexenone 
• 688048-71-7 ((1S,2S,4R)-4,7,7-Trimethyl-3-oxo-bicyclo[2.2.1]hept-2-ylselanyl)-acetic acid methyl ester 
• 86505-46-6 (S)-(+)-2-(p-tolylsulfinyl)-2-cyclohexenone 
• 164931-75-3 (R)-3-[bis(benzyloxycarbonyl)methyl]cyclohexanone 
• 126-39-6 2-ethyl-2-methyl-1,3-dioxolane 
• 164931-77-5 dimethyl 2-((R)-3-oxocyclohexyl)malonate 
• 72049-87-7 ((S)-3-Oxo-cyclohexyl)-trimethylsilanyl-acetic acid methyl ester 

Downstream Products

• 1046466-32-3 C₉H₁₆O₃ 

Relevant academic research and scientific papers

Enantioselective Synthesis and in Vivo Evaluation of Regioisomeric Analogues of the Antimalarial Arterolane

We describe the first systematic study of antimalarial 1,2,4-trioxolanes bearing a substitution pattern regioisomeric to that of arterolane. Conformational analysis suggested that trans-3″-substituted trioxolanes would exhibit Fe(II) reactivity and antipa

Stereoselective synthesis of (+)-2-deoxyolivin based on cycloaddition reaction between the homophthalic anhydride and the chiral cyclohexenone derivative

The olivomycins are representative antitumor antibiotics in the aureolic family of the compounds, which contains the tricyclic aglycon core, olivin. In this study, we established the efficient synthesis of the anthracenone core skeleton based on a cycload

Synthesis of optically active (1R,4S,6S)-6-hydroxybicyclo[2.2.2]octan-2-one

Bicyclo[2.2.2]octanone is an important building block for the synthesis of bioactive compounds and natural products. Herein, we present a new synthetic route for the formation of (1R,4S,6S)-6-hydroxybicyclo[2.2.2]octan-2-one derivatives via a catalytic as

Conjugated additions of selenium containing enolates to enones - Enantioselective synthesis of δ-oxo-α-seleno esters and their facile transformations

Titanium enolates derived from methyl phenylselenoacetate and other acetates bearing a selenium containing chiral auxiliary have been employed to bring about 1,4-addition reactions to enones. These reactions generate δ-oxo-α-seleno esters in good yields and with excellent regio- and diastereoselectivities. The results obtained clearly indicate that the Lewis acids, employed to activate the starting enones towards addition, greatly influence reactivity as well as the stereochemical outcomes of these reactions. TiCl4 complexation resulted in particularly efficient promotion of the 1,4-addition. Simple manipulations of the organoselenium moiety allowed some enantiomerically pure δ-oxo-α-camphorseleno esters to be transformed into the corresponding δ-oxo-α-hydroxy or δ-oxo-α-allyl esters or into trisubstituted tetrahydrofurans. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Asymmetric Michael Addition Reaction of Phosphorus-Stabilized Allyl Anions with Cyclic Enones

The asymmetric Michael addition reaction of chiraly modified P-allyl anions derived from enantiomerically ebriched 2-allyl-1,3,2-oxazaphosphorinane 2-oxides has been investigated with cyclic enones.The racemic 1,3,2-oxazaphosphorinane 2-oxide 3 has been shown to be extremely diastereoselective in the Michael addition to 5-, 6-, and 7-ring enones.With the enantiomerically enriched 2-allyl-1,3,2-oxazaphosphorinane 2-oxides, high regio- and diastereoselectivities (88-90percent diastereomeric excess) have been achieved in the Michael addition reaction of one of the diastereomers (cis series).The Michael reaction of the anions derived from the trans series were not diastereoselective (ca. 10percent diastereomeric excess).The origin of the addition selectivity can be rationalized by (1) consideration of the structure and conformational preferences of the allyl anion (parallel conformation, s-trans, no lithium contact), (2) conformational analysis of the 1,3,2-oxazaphosphorinane 2-oxide ring (chair, equatorial allyl group) and (3) assumption of a 10-membered ring transition state structure with lithium coordination of the enone.

ASYMMETRIC MICHAEL ADDITIONS OF ESTER ENOLATES TO ENANTIOMERICALLY PURE VINYLIC SULFOXIDES SYNTHESIS OF 3-SUBSTITUTED GLUTARATE ESTERS IN HIGH ENANTIOMERIC PURITY

Various ester enolate ions add as Michael donors to enantiomerically pure Michael acceptor cycloalkenone sulfoxides 1a and 1b and unsaturated lactone sulfoxides 3a and 3b.The level of asymmetric induction in some cases is extraordinarily high (>=95percent