142096-81-9Relevant articles and documents
Chiral recyclable fluorous disulfonamide ligand for catalytic enantioselective cyclopropanation of allylic alcohols
Kawashima, Yuya,Ezawa, Tetsuya,Yamamura, Mai,Harada, Taisuke,Noguchi, Takuya,Miura, Tsuyoshi,Imai, Nobuyuki
, p. 8585 - 8592 (2016/01/25)
Allylic alcohols reacted with Et2Zn and CH2I2 in the presence of a catalytic amount of fluorous disulfonamide 3a to afford the corresponding cyclopropylmethanols in 69%-quantitative yields with 49-85% ee. Recovery of the fluorous ligand 3a was readily performed from the reaction mixture by the fluorous solid-phase extraction (FSPE), and the recovered 3a could be reused without a significant loss of the catalytic activity and enantioselectivity.
Catalytic enantioselective cyclopropanation of allylic alcohols using recyclable fluorous disulfonamide ligand
Miura, Tsuyoshi,Itoh, Keisuke,Yasaku, Yumi,Koyata, Naka,Murakami, Yasuoki,Imai, Nobuyuki
, p. 5813 - 5815 (2008/12/22)
Cyclopropanation of allylic alcohols with Et2Zn and CH2I2 in the presence of a catalytic amount of fluorous disulfonamide 3 afforded the corresponding cyclopropylmethanols in 69-96% yield with 49-83% ee. The fluorous ligand 3 was readily recovered from the reaction mixture by the fluorous solid-phase extraction (FSPE) and could be reused without a significant loss of the catalytic activity and enantioselectivity.
N,N,N′,N′-Tetraalkyl-2,2′-dihydroxy-1,1′- binaphthyl-3,3′-dicarboxamides: Novel Chiral Auxiliaries for Asymmetric Simons-Smith Cyclopropanation of Allylic Alcohols and for Asymmetric Diethylzinc Addition to Aldehydes
Kitajima, Hiroshi,Ito, Katsuji,Aoki, Yuko,Katsuki, Tsutomu
, p. 207 - 217 (2007/10/03)
The newly introduced tittle compounds were found to be efficient chiral auxiliaries for the asymmetric Simmons-Smith cyclopropanation of allylic alcohols and for asymmetric addition of diethylzinc to aldehydes. For example, Simmons- Smith cyclopropanation of cinnamyl alcohol in the presence of N,N,N′,N′-tetraethyl-2,2′-dihydroxy-1, 1′-binaphthyl-3, 3′-dicarboxamide (1b) proceeded with high enantioselectivity of 94% ee and addition of diethylzinc to benzaldehyde in the presence of N,N,N′,N′-tetraisopropyl-2,2′-dihydroxy-1,1′-binaphthyl- 3,3′-dicarboxamide (1e) proceeded with enantioselectivity of 99% ee. Although the reaction mechanism of these reactions is still nuclear, a monomeric seven-membered 2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxamide (1)-Zn complex is considered to be an active species which catalyzes the above reactions, on the basis of NMR experiments.
