153861-59-7Relevant articles and documents
Cyclopropane-based conformational restriction of GABA by a stereochemical diversity-oriented strategy: Identification of an efficient lead for potent inhibitors of GABA transports
Nakada, Kazuaki,Yoshikawa, Mamie,Ide, Soichiro,Suemasa, Akihiro,Kawamura, Shuhei,Kobayashi, Takaaki,Masuda, Eiji,Ito, Yoshihiko,Hayakawa, Wataru,Katayama, Takahiro,Yamada, Shizuo,Arisawa, Mitsuhiro,Minami, Masabumi,Shuto, Satoshi
, p. 4938 - 4950 (2013/09/02)
A series of cyclopropane-based conformationally restricted γ-aminobutyric acid (GABA) analogs with stereochemical diversity, that is, the trans- and cis-2,3-methano analogs Ia and Ib and their enantiomers ent-Ia and ent-Ib, and also the trans- and cis-3,4
Synthesis of Optically Active cis- and trans-1,2-Disubstituted Cyclopropane Derivatives by the Simmons-Smith Reaction of Allyl Alcohol Derivatives Derived from (R)-2,3-O-Isopropylideneglyceraldehyde
Morikawa, Tsutomu,Sasaki, Hirofumi,Hanai, Ryo,Shibuya, Akira,Taguchi, Takeo
, p. 97 - 103 (2007/10/02)
The Simmons-Smith reactions of Z- and E-allyl alcohol derivatives 6 derived from (R)-2,3-O-isopropylideneglyceraldehyde (5) were used for the synthesis of optically active cis- and trans-1,2-disubstituted cyclopropane derivatives.Reaction of 6 with diethyl zinc and diiodomethane gave cyclopropane derivatives 7 in 84percent to quantitative yields with 35 to ca. 100percent des.Identical facial selectivities toward the double bonds, 1re-2si for Z-6 and 1re-2re for E-6, were observed in the cyclopropanations.The diastereoselectivity was dependent on the protecting group on the terminal allylic oxygen (R of 6, TBDPS > MOM > Bn) and on the stereochemistry of the double bond (Z > E).For TBDPS ethers Z- and E-6c, cis- and trans-7c were obtained as single diastereomers, respectively.It was clearly demonstrated that the stereoselectivity of the cyclopropanation is controlled by the directing effect of the allylic oxygen (O-1) of the dioxolane ring, which coordinates to the reagent.The terminal allylic oxygen (O-2) lowered the diastereoselectivity.This reaction was applied to the synthesis of optically active cyclopropane analogs of γ-aminobutyric acid (GABA) 18, 22, and ent-22.