- Palladium-catalyzed stereospecific cross-coupling of enantioenriched allylic alcohols with boronic acids
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In the presence of 2.5 mol% Pd2(dba)3-TMEDA (1 : 4), a range of enantioenriched allylic alcohols smoothly coupled with boronic acids in a highly regioselective fashion with inversion of configuration to afford structurally diverse alkenes in good yields with perfect retention of ee.
- Wu, Hai-Bian,Ma, Xian-Tao,Tian, Shi-Kai
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supporting information
p. 219 - 221
(2014/01/06)
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- Studies on angiotensin converting enzyme inhibitors. V. The diastereoselective synthesis of 2-oxoimidazolidine derivatives
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A diastereoselective synthesis of imidapril (1), which is under clinical study as an antihypertensive drug based on its angiotensin converting enzyme (ACE)-inhibitory activity, was established. N-Alkylation of (2S)-2-amino-4-phenylbutyric acid ester (12) with 3-((2R)-2-methane or toluenesulfonyloxypropionyl)-2-oxoimidazolidine derivative (11) diastereoselectively proceeded in an SN2 fashion to afford tert-butyl (4S)-3-[(2S)-2-[N-[(1S)-1-ethoxycarbonyl)-3-phenylpropyl]amino]propionyl]- 1-methyl-2-oxoimidazolidine-4-carboxylate (13), a precursor of 1. Alternatively, benzyl (2S)-2-[N-(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]propionate (15), which is the key building block of 13, was synthesized by the same strategy. This procedure was also applied to the synthesis of enalapril.
- Kubota,Nunami,Yamagishi,Nishimoto,Hayashi
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p. 1374 - 1377
(2007/10/02)
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