134931-64-9Relevant articles and documents
Enantioselective Darzens reaction: Asymmetric synthesis of trans-glycidic esters mediated by chiral lithium amides
Takahashi,Muraoka,Capo,Koga
, p. 1821 - 1823 (1995)
Enantioselective and diastereoselective Darzens reaction mediated by chiral lithium amides was achieved between tert-butyl chloroacetate and aromatic aldehydes to give the corresponding trans-glycidic esters in up to 84% enantiomeric excess.
Efficient alternative synthetic route to diltiazem via (2R,3S)-3-(4- methoxyphenyl)glycidamide
Yamada, Shin-ichi,Tsujioka, Ikuko,Shibatani, Takeji,Yoshioka, Ryuzo
, p. 146 - 150 (2007/10/03)
An effective new route to diltiazem, a representative coronary vasodilator, through (-)-(2R,3S)-3-(4-methoxyphenyl)glycidamide [(-)-2] has been achieved. The glycidamide (-)-2 was prepared in 43% overall yield by a combination of the enzymatic resolution of methyl (±)2(2RS,3SR)-3-(4- methoxyphenyl)glycidate [(±)-1] with lipase and the following amidation of (-)-1 with ammonia. A one-pot synthesis through the treatment of (-)-2 with 2-aminothiophenol and a following ring closing reaction efficiently gave a key intermediate of diltiazem synthesis, (2S,3S)-2,3-dihydro-3-hydroxy-2-(4- methoxyphenyl)-1,5-benzothiazepin-4(5H)-one [cis-(+)-5] in 80% overall yield.
Reactions of Methyl threo-2-Acetoxy-3-chloro-3-(4-methoxyphenyl)propanoate and Methyl cis-2,3-Epoxy-3-(4-methoxyphenyl)propanoate with 3,5-Dimethoxyphenol: Potential Routes to Flavan-3-ols
Brown, Roger. F. C.,Jackson, W. Roy,McCarthy, Tom D.,Fallon, Gary D.
, p. 1833 - 1843 (2007/10/02)
Attempted syntheses of flavan-3-ols by reaction of either methyl threo-2-acetoxy-3-chloro-3-(4-methoxyphenyl)propanoate (3) or methyl cis-2,3-epoxy-3-(4-methoxyphenyl)propanoate (14) with 3,5-dimethoxyphenol failed to give the required aryl ethers.Products usually were derived from C-alkylation of the electron-rich phenol although reaction of the chloro acetate (3) with the phenoxide ion gave the furanone (5).The single-crystal X-ray structures of methyl 4-hydroxy-3-(4-methoxyphenyl)-2-(4-methoxyphenylmethyl)-5-oxo-2,5-dihydrofuran-2-carboxylate and cis-3-hydroxy-5,7-dimethoxy-4-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-2-one have been determined.