title: One-Pot Synthesis of (S)-Baclofen via Aldol Condensation of Acetaldehyde with Diphenylprolinol Silyl Ether Mediated Asymmetric Michael Reaction as a Key Step.
abstract: An efficient asymmetric total synthesis of (S)-baclofen was accomplished via a one-pot operation from commercially available materials using sequential reactions, such as aldol condensation of acetaldehyde, diphenylprolinol silyl ether mediated asymmetric Michael reaction of nitromethane, Kraus-Pinnick oxidation, and Raney Ni reduction. Highly enantioenriched baclofen was obtained in one pot with a good yield over four reactions.
authors.affiliation: Department of Chemistry, Graduate School of Science, Tohoku University , 6-3 Aramaki-Aza Aoba-ku, Sendai, Miyagi 980-8578, Japan.
authors.forename: Yujiro
authors.initials: Y
authors.lastname: Hayashi
authors.affiliation: Department of Chemistry, Graduate School of Science, Tohoku University , 6-3 Aramaki-Aza Aoba-ku, Sendai, Miyagi 980-8578, Japan.
authors.forename: Daisuke
authors.initials: D
authors.lastname: Sakamoto
authors.affiliation: Department of Chemistry, Graduate School of Science, Tohoku University , 6-3 Aramaki-Aza Aoba-ku, Sendai, Miyagi 980-8578, Japan.
authors.forename: Daichi
authors.initials: D
authors.lastname: Okamura
mesh_terms: D000079:Acetaldehyde / Q000737:chemistry*; D000447:Aldehydes; D001418:Baclofen / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004987:Ethers / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D009595:Nitroparaffins / Q000737:chemistry; D010084:Oxidation-Reduction; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D004987:Ethers; D009595:Nitroparaffins; C529940:diphenylprolinol silyl ether; C116609:3-hydroxybutanal; D011392:Proline; D000079:Acetaldehyde; D001418:Baclofen; D008697:Methane; C008640:nitromethane