Title: Synthesis of Enantiopure 3-Quinuclidinone Analogues with Three Stereogenic Centers: <i>(1S,2R,4S)-</i> and <i>(1S,2S,4S)</i>-2-(Hydroxymethyl)-1-azabicyclo[2.2.2]octan-5-one and Stereocontrol of Nucleophilic Addition to the Carbonyl Group
Abstract:The pseudoenantiomeric title compounds have been prepared from quincorine (QCI) and quincoridine (QCD), respectively, in enantiopure form following an efficient six-step pathway. Nucleophilic attack a...The pseudoenantiomeric title compounds have been prepared from quincorine (QCI) and quincoridine (QCD), respectively, in enantiopure form following an efficient six-step pathway. Nucleophilic attack at the carbonyl group proceeds preferentially from the supposedly more hindered endo pi-face, giving quinuclidinols with natural configuration at C5 (up to 97%). pi-Face selectivity is highest in the QCD series with bulky O-protecting groups, involving an unprecedented 1,7-stereoinduction.Read More
Publication Year: 2000
Publication Date: 2000-06-01
Language: en
Type: article
Indexed In: ['crossref', 'pubmed']
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Cited By Count: 16
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