77312-71-1Relevant articles and documents
One-pot cascade synthesis of azabicycles via the nitro-Mannich reaction and N -alkylation
Disadee, Wannaporn,Ruchirawat, Somsak
supporting information, p. 707 - 711 (2018/02/09)
A one-pot, metal-free process for the synthesis of azabicycles is developed. The key transformations involved a cascade of double intramolecular cyclizations via the nitro-Mannich reaction and N-alkylation, providing various ring systems of azabicycles in
Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H
Vulovic, Bojan,Kolarski, Dusan,Bihelovic, Filip,Matovic, Radomir,Gruden, Maja,Saicic, Radomir N.
supporting information, p. 3886 - 3889 (2016/08/16)
1,6-Diynes with a t-butylcarbonate group in the propargylic position undergo gold(I)-catalyzed domino-cyclization which affords α-hydroxycyclohexenones. The described sequence can be applied on functionalized, highly oxygenated substrates, as examplified
Asymmetric synthesis of gem-difluoromethylenated dihydroxypyrrolizidines and indolizidines
Thaharn, Watcharaporn,Bootwicha, Teerawut,Soorukram, Darunee,Kuhakarn, Chutima,Prabpai, Samran,Kongsaeree, Palangpon,Tuchinda, Patoomratana,Reutrakul, Vichai,Pohmakotr, Manat
, p. 8465 - 8479,15 (2020/09/15)
An asymmetric synthesis of gem-difluoromethylenated dihydroxypyrrolizidines and indolizidines is described. The fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 (1) to chiral imides was achieved in satisfactory yields to provide mixtures of syn- and anti-isomers 6-9 with moderate to good diastereoselectivities. Reductive cleavage of the phenylsulfanyl group followed by intramolecular radical cyclization of the syn-isomers 6-9 occurred under refluxing conditions to afford the corresponding gem-difluoromethylenated 1-azabicyclic compounds 10-13 in moderate yields as a separable mixture of cis- and trans-isomers. The cis-isomers of compounds 10 and 12 and trans-13 were readily transformed to gem-difluoromethylenated dihydroxypyrrolizidines 20 and 27 and indolizidine 28, respectively, by reductive cleavage of the hydroxyl group and organometallic addition followed by hydrogenolysis.
