The preparation of novel chiral auxiliaries SAMIQ/RAMIQ and their application in the asymmetric Michael addition |
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| Authors: | Xuan Pan Zhanzhu Liu |
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| Affiliation: | State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, PR China |
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| Abstract: | ![]()
A pair of novel chiral auxiliaries SAMIQ/RAMIQ was synthesized from l- or d-phenylalanine methyl ester hydrochloride over six steps in 45.8% and 44.4% yield, respectively. The SAMIQ-/RAMIQ-hydrazone methodology was applied for the asymmetric Michael addition of ketones to α,β-unsaturated carboxylic acid methyl esters, which afforded 3-substituted-5-oxo-alkanoates in moderate to good yield (65–82%) with excellent enantioselectivity (ee=95.3%∼>99.5%). |
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| Keywords: | Chiral auxiliary SAMIQ/RAMIQ Asymmetric Michael addition |
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