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dc.contributor.author郑啸
dc.contributor.author陈果
dc.contributor.author阮源萍
dc.contributor.author黄培强
dc.date.accessioned2016-05-17T02:56:48Z
dc.date.available2016-05-17T02:56:48Z
dc.date.issued2009
dc.identifier.citation中国科学(B辑:化学),2009,(10):179-187
dc.identifier.issn1006-9240
dc.identifier.otherJBXK200910016
dc.identifier.urihttps://dspace.xmu.edu.cn/handle/2288/107839
dc.description.abstract合成了(S)-3-羟基哌啶苯硫醚化合物6作为3-羟基哌啶氮α-碳负离子手性合成子(b)的合成等效体.化合物6经羟基去质子现场保护、萘锂(ln)还原锂化形成手性哌啶醇双负离子中间体b.双负离子b可被质子淬灭得到还原产物2A;而与羰基化合物反应则得到α-羟烷化产物12~17和少量还原产物2A.该反应具有很高的环上2,3-位非对映立体选择性;与非对称的羰基化合物反应产生新手性中心的立体选择性从50:50到77:23.
dc.description.abstractThe (S)-sulfide 6 was synthesized as a synthetic equivalent of novel 3-piperidinol N-α-carbanion B, viadeprotonation and lithium naphthanelide (LN)-mediated reductive lithiation.The reaction of the 3-piperidinolN-α-carbanion intermediate B with carbonyl compounds gave, besides some reduced product 2a, the desiredα-hydroxyalkylation products 12~17 with excellent 2,3-diastereoselectivity.The reductive α-hydroxyalkylation withunsymmetric carbonyl compounds led to only 50:50 to 77:23 diastereoselectivities at the C-1’ carbinol center.
dc.description.sponsorship国家自然科学基金(批准号:20832005)资助
dc.language.isozh_CN
dc.subject苯硫醚
dc.subject氮α位碳负离子
dc.subject还原锂化
dc.subjectα-羟烷化
dc.subject非对映立体选择性
dc.subjectsulfide
dc.subjectN-α-carbanion
dc.subjectlithium-naphthanelide
dc.subjectreductive lithiation
dc.subjectcarbonyl compounds
dc.subjectα-hydroxyal-kylation
dc.subjectdiastereoselectivity
dc.title3-羟基哌啶氮α-碳负离子的形成及α-羟烷化反应
dc.title.alternativeGeneration and α-hydroxyalkylation of a Novel 3-piperidinol N-α-carbanion intermediate
dc.typeArticle


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