Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: Boc-D-Prolinol, is researched, Molecular C10H19NO3, CAS is 83435-58-9, about Complex Induced Proximity Effects: Enantioselective Syntheses Based on Asymmetric Deprotonations of N-Boc-pyrrolidines.SDS of cas: 83435-58-9.
Lithiation of N-Boc-pyrrolidine (I) with sec-butyllithium (s-BuLi)/(-)-sparteine (II) effects an asym. deprotonation to give (S)-2-lithio-N-Boc-pyrrolidine, which reacts with electrophiles to provide the 2-substituted N-Boc-pyrrolidines in enantiomeric excesses which generally are >90%. In the lithiation-silylation of I with the chiral ligand III gives IV with a lower enantiomeric excess. Diastereoselective amplification operates in a sequential lithiation-substitution sequence to provide the conversion of (S)-2-methyl-N-Boc-pyrrolidine of 95% enantiomeric excess with s-BuLi/II to (S,S)-2,5-dimethyl-N-Boc-pyrrolidine ((S,S)-19) with >99% enantiomeric excess. Synthetic preparations of a useful chiral ligand, (R)-α,α-diphenyl-2-pyrrolidine, and a useful chiral auxiliary, (S,S)-2,5-dimethylpyrrolidine hydrochloride, are reported. Reactions of racemic and enantioenriched 2-lithio-N-Boc-pyrrolidine and investigation of sequential lithiations-deuterations of I establish the reaction pathway to be asym. deprotonation rather than asym. substitution. A rationalization for the enantioselective deprotonation is provided.
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Reference:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica