1037302-75-2Relevant academic research and scientific papers
Asymmetric michael addition of a recyclable chiral amine: Inversion of stereoselectivity caused by the difference of ethereal solvents
Node, Manabu,Hashimoto, Daisuke,Katoh, Takahiro,Ochi, Shunsuke,Ozeki, Minoru,Watanabe, Tsunefumi,Kajimoto, Tetsuya
, p. 2653 - 2656 (2008)
(Chemical Equation Presented) The Michael addition of a chiral amine [(-)-6] to α,β-unsaturated esters (4) was attained and the stereoselectivity was inverted by changing the solvent from diethyl ether to tetrahydrofuran when α,β-unsaturated esters having an aromatic ring at the β-position were employed. In addition, the chiral auxiliary in the Michael adducts (9A) was facilely removed with N-iodosuccinimide to afford β-amino esters (10A) and 2-methoxy-d-bornylaldehyde (11), which can be reclaimed to the chiral amine (6) by reductive amination.
