105873-83-4Relevant academic research and scientific papers
Asymmetric Synthesis Using Chiral Acetals: Studies on the Nucleophilic Addition of Organometallics to Chiral α-Keto Acetals in Cyclic Systems
Tamura, Yasumitsu,Annoura, Hirokazu,Kondo, Hiroshi,Fuji, Masahiro,Yoshida, Takayuki,Fujioka, Hiromichi
, p. 2305 - 2313 (2007/10/02)
Four chiral cyclic α-keto acetals (3a-d) were prepared through transacetalization of the α-hydroxydimethyl acetals with (-)-(2S,3S)-1,4-dimethoxy-2,3-butanediol or (-)-(2R,3R)-2,3-butanediol and reacted with organometallic reagents (Grignard reagents and organolithium reagents).The reactions of the α-keto acetals (3a, 3b) derived from 1 and (-)-(2S,3S)-1,4-dimethoxy-2,3-butanediol with Grignard reagents proceeded in a highly diastereoselective manner.Keywords-Asymmetric synthesis; diastereoselective nucleophilic addition; chiral cyclic α-keto-acetal; (-)-(2S,3S)-1,4-dimethoxy-2,3-butanediol; (-)-(2R,3R)-2,3-butanediol; Grignard reagent; organolithium reagent
DIASTEREOSELECTIVE ADDITION OF GRIGNARD REAGENTS TO CHIRAL α-KETOACETALS
Tamura, Yasumitsu,Kondo, Hiroshi,Annoura, Hirokazu,Takeuchi, Ritsuko,Fujioka, Hiromichi
, p. 81 - 82 (2007/10/02)
High diastereoface-differenciating addition occured in the reaction of chiral cyclic α-ketoacetals 1a and 1b with Grignard reagents.
