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Chiral 2-(2-hydroxyaryl)alcohols (HAROLs) with a 1,4-diol scaffold as a new family of ligands and organocatalysts
Tetrahedron ( IF 2.1 ) Pub Date : 2017-11-22 , DOI: 10.1016/j.tet.2017.11.054
Ömer Dilek , Mustafa A. Tezeren , Tahir Tilki , Erkan Ertürk

Efficient and modular syntheses of chiral 2-(2-hydroxyaryl)alcohols (HAROLs), novel 1,4-diols carrying one phenolic and one alcohol hydroxyl group, have been developed which led to generation of a small library of structurally diverse HAROLs in enantiomerically pure form. Of the different HAROLs examined, a HAROL based on the indan backbone exhibited the highest activity and enantioselectivity in the 1,2-addition of certain organometallic compounds to aldehydes in the presence of Ti(OiPr)4 (up to 97% y, 88% ee) and performed as a hydrogen-bond donor organocatalyst in the Morita-Baylis-Hillman reaction, promoted by trialkylphosphines.



中文翻译:

具有1,4-二醇骨架的手性2-(2-羟基芳基)醇(HAROLs)作为新的配体和有机催化剂家族

高效和模块化的手性2-(2-羟基芳基)醇(HAROLs)的合成,带有一个酚和一个醇羟基的新型1,4-二醇已被开发出来,这导致在对映异构体中生成结构多样的HAROLS小文库纯形式。在考察的不同HAROL中,基于茚满骨架的HAROL在Ti(O i Pr)4y高达97%, 88%ee)并在三田膦的促进下在Morita-Baylis-Hillman反应中作为氢键供体有机催化剂发挥作用。

更新日期:2017-11-22
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