102860-22-0Relevant academic research and scientific papers
A versatile and concise route to carbocycles using a 1,6-electrocyclic reaction
Brandaenge, Svante,Leijonmarck, Hans
, p. 292 - 293 (2007/10/03)
The viability of the 1,6-electrocyclic route to 1,3-cyclohexadienes has been significantly increased by using a phenyl-sulfonyl substituent in a multi-purpose (≥3) role.
Improved and environmentally friendly large-scale preparation of cyclohexadienyl-, cycloheptadienyl sulfone and enantiopure epoxy cycloheptyl sulfones
Park, Taesik,Torres, Eduardo,Fuchs, Philip L.
, p. 1895 - 1900 (2007/10/03)
Kilogram-scale amounts of cycloheptadienyl phenylsulfone and cyclohexadienyl phenylsulfone were prepared by one operation in 5 stages with over 50% yield and requiring no purification. A practical and efficient method for the Jacobsen asymmetric epoxidati
Economical and environmentally friendly syntheses of 2-(phenylsulfonyl)-1,3-cyclohexadiene and 2-(phenylsulfonyl)-1,3-cycloheptadiene
Meyers, David J.,Fuchs, Philip L.
, p. 200 - 204 (2007/10/03)
A large-scale and inexpensive synthesis of dienes 1 and 2 has been developed via a four-step procedure starting with benzenethiol and the corresponding cyclic ketone. No chromatography is required.
Polystyrene-supported selenosulfonates: Efficient reagents for regio- and stereocontrolled synthesis of vinyl sulfones
Qian,Huang
, p. 1913 - 1916 (2007/10/03)
Two novel polystyrene-supported selenosulfonates reagents have been developed. As reagents for boron trifluoride catalyzed or AIBN catalyzed addition to olefins were successfully demonstrated and have been used for regioselective synthesis of vinyl sulfon
BF3-induced rearrangement of aziridino cyclopropanes derived from 2-phenylsulfonyl 1,3-dienes. Application to the total synthesis of (±)-ferruginine
Jonsson,Loefstroem,Baeckvall
, p. 8454 - 8457 (2007/10/03)
Total synthesis of the alkaloid (±)-ferruginine (1) has been developed via the 2-phenylsulfonyl 1,3-diene approach. BF3-induced rearrangement of the N-protected cyclohexane aziridino cyclopropane 8, derived from its corresponding epoxy cyclopropane, afforded the desired tropane alkaloid skeleton 9 in good yield. Michael addition of nitroethane (as an acyl anion equivalent) and transformation of the nitro group of the adduct 10 to a keto function gave 11. Elimination of benzenesulfinic acid and subsequent replacement of the tosyl group by a methyl group afforded the title compound 1.
SELENOSULFONATION OF 1,3-DIENES: ONE-POT SYNTHESIS OF 2-(PHENYLSULFONYL)-1,3-DIENES
Baeckvall, Jan-E.,Najera, Carmen,Yus, Miguel
, p. 1445 - 1448 (2007/10/02)
A one-pot procedure for the transformation of a 1,3-diene into the corresponding 2-(phenylsulfonyl)-1,3-diene was developed.The reaction involves a 1,2-selenosulfonation-oxidation sequence.
SULFONYLMERCURATION OF CONJUGATED DIENES. A FACILE ROUTE TO ALLYL- AND DIENYL-SULFONES
Andell, Ove S.,Baeckvall, Jan-E.
, p. 4555 - 4558 (2007/10/02)
Phenylsulfonylmercuration of 1,3-dienes gives mercury adducts, which on treatment with base afford phenylsulfonyldienes.In most cases the reaction proceeds regioselectively to give 2-(phenylsulfonyl)-1,3-dienes.These are useful synthetic intermediates and
