Oxazolines. 2. 2-Substituted 2-oxazolines as synthons for N-(. beta.-hydroxyethyl) arylalkylamines, intermediates in a synthesis of 1, 2, 3, 4-tetrahydroisoquinolines …

LN Pridgen, LB Killmer, RL Webb

Index: Pridgen, Lendon N.; Killmer, Lewis B.; Webb, R. Lee Journal of Organic Chemistry, 1982 , vol. 47, # 11 p. 1985 - 1989

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Citation Number: 31

Abstract

2-(Arylalkyl)-2-oxazolines 4 (n= 1) and 2-aryl-2-oxazolines 4 (n= 0), the latter prepared in a novel reaction by cross-coupling aryl Grignard reagents with 2-(methylthio)-5-phenyl-2- oxazoline(10) and using [1, l'-bis (di-phenylphosphino) ferrocene] palladium (II) chloride (14) as a catalyst, were reduced in a previously unreported reaction by diborane in refluxing THF to yield N-((3-hydroxyethy1) arylalkylamines 5 (n= 1, 2). Amino alcohols 5 were cyclized to ...

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