用于前手性脂肪族酮不对称还原胺化的钛（IV）醇盐和雷尼镍的演变

Evolution of titanium(IV) alkoxides and raney nickel for asymmetric reductive amination of prochiral aliphatic ketones.

作者信息

Nugent Thomas C, Wakchaure Vijay N, Ghosh Abhijit K, Mohanty Rashmi R

机构信息

Department of Chemistry, School of Engineering and Science, International University Bremen, Germany.

出版信息

Org Lett. 2005 Oct 27;7(22):4967-70. doi: 10.1021/ol051909v.

DOI:10.1021/ol051909v

PMID:16235934

Abstract

[reaction: see text] A new method for the one-pot asymmetric reductive amination of prochiral aliphatic ketones has been developed. The previously unexplored reagent combination of Ti(O(i)Pr)(4)/Raney Ni/H(2) in the presence of (R)- or (S)-alpha-methylbenzylamine provides good to excellent yield (76-90%) and diastereomeric excess (72-98%). The second step, hydrogenolysis, provides the corresponding primary amine in high yield (88-93%) and with uncompromised enantiomeric excess.

摘要

[反应：见正文] 已开发出一种用于前手性脂肪族酮一锅法不对称还原胺化的新方法。在（R）-或（S）-α-甲基苄胺存在下，Ti（O（i）Pr）4/阮内镍/H2这种先前未被探索的试剂组合可提供良好至优异的产率（76 - 90%）和非对映体过量（72 - 98%）。第二步，氢解反应以高产率（88 - 93%）提供相应的伯胺，且对映体过量不受影响。