氯霉素衍生噁唑烷酮的合成及其在Aldol反应中的不对称诱导作用
收稿日期: 2015-04-14
修回日期: 2015-04-27
网络出版日期: 2015-05-06
基金资助
国家自然科学基金(No. 21272279)资助项目.
Synthesis of Oxazolidinone Derivative from Chloramphenicol and Its Asymmetric Induction in Aldol Reaction
Received date: 2015-04-14
Revised date: 2015-04-27
Online published: 2015-05-06
Supported by
Project supported by the National Natural Science Foundation of China (No. 21272279).
以氯霉素为原料, 经五步反应合成了一种新的噁唑烷酮手性辅基, 考察了其在不对称aldol反应中的手性诱导作用. 在TiCl4/N,N'-四甲基乙二胺(TMEDA)存在下, 带有该辅基的酰亚胺烯醇供体可与芳香醛、脂肪醛和α,β-不饱和醛等多种醛顺利反应, 以较高的产率(>80%)和非对映选择性(dr≥19:1)生成Evans型syn-aldol反应产物.
关键词： 氯霉素; 噁唑烷酮手性辅基; 不对称Aldol反应
李薇 , 李云峰 , 俞晓明 . 氯霉素衍生噁唑烷酮的合成及其在Aldol反应中的不对称诱导作用[J]. 有机化学, 2015 , 35(8) : 1657 -1664 . DOI: 10.6023/cjoc201504021
A new oxazolidinone chiral auxiliary was prepared from chloramphenicol in 5 steps. Aldol reactions between enolates bearing this auxiliary and varied aldehydes in the presence of TiCl4/N,N'-tetramethylethalenediamine (TMEDA) were found to proceed in high yield (>80%) and diastereoselectivity (dr≥19:1) to give Evans syn-aldol adducts.
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