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Synthesis of Diastereomeric Bis(oxazoline) Ligands Derived from (S,S)-1,1′-Bis(4-isopropyloxazolin-2-yl)ferrocene
Synlett ( IF 2 ) Pub Date : 2018-01-15 , DOI: 10.1055/s-0036-1589163
Christopher Richards , Ross Arthurs

Starting from ( S , S )-1,1′-bis(4-isopropyloxazolin-2-yl)ferrocene, all possible 2-trimethylsilyl- and 2,2′-di(trimethylsilyl)-substituted diastereoisomers, potential bisoxazoline ligands for use in asymmetric catalysis, were synthesised by selective lithiation followed by addition of trimethylsilyl chloride. Access to the ( S , S , R p , R p )-diastereoisomer was achieved following diastereoselective introduction of two deuterium-blocking groups and utilisation of the high k H / k D value for lithiation, methodology that was also applied to the synthesis of a related 2,2′-di(diphenylmethanol)bisoxazoline ligand.

中文翻译:

(S,S)-1,1'-双(4-异丙基恶唑啉-2-基)二茂铁衍生的非对映双(恶唑啉)配体的合成

从 ( S , S )-1,1'-双(4-异丙基恶唑啉-2-基)二茂铁开始,所有可能的2-三甲基甲硅烷基-和2,2'-二(三甲基甲硅烷基)-取代的非对映异构体,潜在的双恶唑啉配体使用在不对称催化下,通过选择性锂化,然后加入三甲基氯硅烷来合成。在非对映选择性引入两个氘封闭基团并利用高 k H / k D 值进行锂化后,获得了 ( S , S , R p , R p )-非对映异构体,该方法也适用于合成相关的 2,2'-二(二苯基甲醇)双恶唑啉配体。
更新日期:2018-01-15
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