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二环己基氯硼烷诱导的 L-赤藓糖衍生物与手性醛之间的反 aldol 反应中的双重非对映选择性。

Double diastereoselection in anti aldol reactions mediated by dicyclohexylchloroborane between an L-erythrulose derivative and chiral aldehydes.

机构信息

Depart. de Q. Inorgánica y Orgánica, Univ. Jaume I, Castellón, E-12071 Castellón, Spain.

出版信息

Org Biomol Chem. 2012 Sep 14;10(34):6937-44. doi: 10.1039/c2ob25803j. Epub 2012 Jul 24.

DOI:10.1039/c2ob25803j
PMID:22825403
Abstract

Anti aldol reactions of an l-erythrulose derivative with several α-chiral aldehydes mediated by dicyclohexylboron chloride are examined. Good yields and stereoselectivities are observed. The results are best explained when the reactions are assumed to occur via boat-like transition states with minimization of 1,3-allylic strain and avoidance of syn pentane interactions.

摘要

对 l-赤藓糖衍生物与几种α-手性醛在二环己基氯化硼作用下的反aldol 反应进行了考察。观察到了良好的产率和立体选择性。当反应被假设通过船型过渡态进行，以最小化 1,3-烯丙基应变并避免顺戊烷相互作用时，反应结果得到了最好的解释。

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