71055-13-5Relevant academic research and scientific papers
Four-Step One-Pot Catalytic Asymmetric Synthesis of Polysubstituted Tricyclic Compounds: Lipase-Catalyzed Dynamic Kinetic Resolution Followed by an Intramolecular Diels-Alder Reaction
Tsuchimochi, Izuru,Hori, Shuhei,Takeuchi, Yasuo,Egi, Masahiro,Satoh, Tomo-O,Kanomata, Kyohei,Ikawa, Takashi,Akai, Shuji
supporting information, p. 822 - 828 (2021/02/16)
Starting from readily available tertiary alcohols, four different reactions (a 1,3-migration of a hydroxy group, kinetic resolution, racemization, and an intramolecular Diels-Alder reaction) took place under co-catalysis by lipase and oxovanadium compounds in a one-pot process to produce polysubstituted tricyclic carbon frameworks in high yields and with high enantioselectivities. The key to the success of this process was the discovery that a silyl group attached to the terminal carbon of the vinyl moiety completely controls the direction of hydroxy group migration.
Thermal reactions of anti- and syn-dispiro[5.0.5.2]tetradeca-1,8-dienes: Stereomutation and fragmentation to 3-methylenecyclohexenes. Entropy-dictated product ratios from diradical intermediates?
Doering,Ekmanis,Belfield,Klaerner,Krawczyk
, p. 5532 - 5541 (2007/10/03)
A series of cyclobutanes substituted 1,2- by polyenes of increasing radical-stabilizing power has been investigated to test the proposition that stabilization energies obtained independently from apposite, cis,-trans geometric isomerizations can be succes
STEREOSTRUCTURE OF RENGYOL AND ISORENGYOL, PHENYLETHANOIDS OF FORSYTHIA SUSPENSA
Endo, Katsuya,Seya, Kazuhiko,Hikino, Hiroshi
, p. 2681 - 2688 (2007/10/02)
Determination of the stereostructure of rengyol (1), a novel nonaromatic phenylethanoid natural product isolated from Forsythia suspensa, by synthetic means has been described.The Reformatsky reaction of 4-acetoxycyclohexanone with ethyl bromoacetate afforded two isomeric acetoxy esters (5, 6) and the one (5) which has an equatorial acetoxyl group yielded on LAH reduction a triol identified as rengyol (1).The isomer (7), obtained similarly from the other isomeric acetoxy ester (6), has also been isolated from the natural source and is named isorengyol.Further, dehydratation of the esters (5, 6) and subsequent pyrolytic deacetoxylation afforded a 1,3-cyclohaxadiene derivative (12), which on photosensitized cis-dioxygenation, followed by reduction, yielded rengyol (1) establishing its stereostructure to have 1,4-cis-cyclohexanediol system.These results supported the previous conclusion based on the 1H and 13C NMR spectral data.
Conversion of 2-Sulfinylated 2-Alkenoate Esters to (2E,4E)-2,4-Alkadienoate Esters by Pyrolysis
Tanikaga, Rikuhei,Nozaki, Yoshihito,Nishida, Masaharu,Kaji, Aritsune
, p. 729 - 733 (2007/10/02)
Thermal reaction of ethyl (2E)-2-phenylsulfinyl-2-alkenoates (E-2) prepared from aldehydes and ethyl 2-phenylsulfinylacetate have been investigated.Refluxing of E-2 or their Z-isomers in xylene resulted in the formation of ethyl (2E,4E)-2,4-alkanedioates accompanied by ethyl (2E)-4-hydroxy-2-alkenoates.Ethyl 2-cycloalkylidene-2-phenylsulfinylacetates were found to be more susceptible to pyrolysis.The enoate esters (2) undergo migration of their carbon-carbon double bond and then sigmatropic rearrangement to benzenesulfenate esters, followed by thermolytic extrusion of a benzenesulfenic acid probably via ethyl(2E)-4-phenylsulfinyl-2-alkenoates to afford ethyl (2E,4E)-2,4-alkadienoates.
