Soeta Takahiro, Kuriyama Masami, Tomioka Kiyoshi
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
J Org Chem. 2005 Jan 7;70(1):297-300. doi: 10.1021/jo0484225.
Asymmetric conjugate addition of dialkylzinc to alpha,beta-unsaturated N-2,4,6-triisopropylphenylsulfonylaldimines 9 was catalyzed by 5 mol % N-Boc-L-valine-connected amidophosphane 5a-Cu(MeCN)(4)BF(4) in the presence of 4 angstroms MS in toluene to afford, after hydrolysis of an imine to an aldehyde through a short alumina column and reduction with sodium borohydride, the corresponding beta-alkylated alkanols 10 with 67-91% ee in reasonably high yields.
在甲苯中，5 mol%的N-Boc-L-缬氨酸连接的氨基膦5a-Cu(MeCN)₄BF₄在4 Å分子筛存在下催化二烷基锌对α,β-不饱和N-2,4,6-三异丙基苯磺酰醛亚胺9的不对称共轭加成反应。通过短氧化铝柱将亚胺水解为醛，然后用硼氢化钠还原，以相当高的产率得到相应的β-烷基化链烷醇10，对映体过量值为67-91%。
