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Asymmetric Michael addition of a recyclable chiral amine: inversion of stereoselectivity caused by the difference of ethereal solvents
Authors:Node Manabu  Hashimoto Daisuke  Katoh Takahiro  Ochi Shunsuke  Ozeki Minoru  Watanabe Tsunefumi  Kajimoto Tetsuya
Affiliation:Department of Pharmaceutical Manufacturing Chemistry, 21st COE program, Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan. node@mb.kyoto-phu.ac.jp
Abstract:The Michael addition of a chiral amine [(-)- 6] to alpha,beta-unsaturated esters ( 4) was attained and the stereoselectivity was inverted by changing the solvent from diethyl ether to tetrahydrofuran when alpha,beta-unsaturated esters having an aromatic ring at the beta-position were employed. In addition, the chiral auxiliary in the Michael adducts ( 9A) was facilely removed with N-iodosuccinimide to afford beta-amino esters ( 10A) and 2-methoxy- d-bornylaldehyde ( 11), which can be reclaimed to the chiral amine ( 6) by reductive amination.
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