- Metal-free visible-light-promoted C(sp3)-H functionalization of aliphatic cyclic ethers using trace O2
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Presented is a light-promoted C-C bond forming reaction yielding sulfone and phosphate derivatives at room temperature in the absence of metals or photoredox catalyst. This transformation proceeds in neat conditions through an auto-oxidation mechanism which is maintained through the leaching of trace amounts of O2 as sole green oxidant. This journal is
- Blackburn, Bryan G.,Cooke, Maria Victoria,Laulhé, Sébastien,Niu, Ben,Sachidanandan, Krishnakumar
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supporting information
p. 9454 - 9459
(2021/12/09)
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- The first examples of rhodium-catalyzed 1,4-conjugate addition reactions of arylboronic acids with ethenesulfonamides
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An unprecedented rhodium-catalyzed 1,4-conjugate addition of arylboronic acids with ethenesulfonamides resulting in the corresponding 2-arylethanesulfonamides is described. The amino substituent, the applied arylboronic acid, the type of Rh-catalyst, and the experimental conditions all affected the reaction outcome.
- Zilaout, Hicham,Van Den Hoogenband, Adri,De Vries, Jelle,Lange, Jos H.M.,Terpstra, Jan Willem
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scheme or table
p. 5934 - 5939
(2011/11/29)
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- Process for synthesis of optically pure prostaglandin E2 and analogs thereof
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The invention comprises a multi-step synthesis of l(-) prostaglandin E2. The special features of the synthesis include: (1) a triply-convergent conjugate-addition and alkylation reaction involving the 1,4-addition of a chiral vinyl lithium reagent to a chiral vinylsulfone to produce a sulfone-stabilized anion. This anion is alkylated in situ to produce the basic prostaglandin skeleton structure, which is then subjected to (2) an efficient peracid oxidation of a secondary amine to a β-silyloxy oxime; and (3) an alkali-catalyzed 1,4-elimination of an α-sulfonyl oxime to produce a vinyl nitroso intermediate. This intermediate is treated with borohydride to give a stereospecific 1,4-reduction which yields the bis-silyloxy oxime of l(-)PGE2. Hydrolysis of the oxime, with concurrent cleavage of the silyloxy protecting groups, affords l(-)PGE2.
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