N-乙酰-(S)-4-异丙基-1-[(R)-1-苯乙基]咪唑烷-2-酮的乙酸醛缩合反应中选择性的反转。

Reversal of selectivity in acetate aldol reactions of N-acetyl-(S)-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one.

机构信息

Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, Mohali, Punjab 160 062, India.

出版信息

Org Lett. 2012 May 18;14(10):2442-5. doi: 10.1021/ol300949s. Epub 2012 May 9.

DOI:10.1021/ol300949s

PMID:22571237

Abstract

Synergistic effects of the exo- and endocyclic chiral centers of an imidazolidinone-based auxiliary were investigated in the perspective of acetate aldol reactions. The reversal in diastereoselectivity was accomplished by lithium and titanium enolate reactions, which proceed through proposed open and closed transitions states, respectively. The aldol adducts were used in the stereoselective synthesis of fluoxetine.

摘要

从乙酰乙酸酯的 aldol 反应的角度出发，研究了基于咪唑烷酮的辅助剂中环外和环内手性中心的协同效应。通过锂和钛烯醇化物反应，可以完成非对映选择性的反转，这两种反应分别通过所提出的开环和闭环过渡态进行。aldol 加成物被用于氟西汀的立体选择性合成。