Enantioselective synthesis of 2-arylpiperidines from chiral lactams.: A concise synthesis of (-)-anabasine
Enantioselective synthesis of 2-arylpiperidines from chiral lactams.: A concise synthesis of (-)-anabasine
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DOI：
10.1039/b200020m
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发表时间：
2002-01-01
影响因子：
4.9
通讯作者：
Bosch, J
中科院分区：
文献类型：
--
作者：
Amat, M;Cantó, M;Bosch, J
用（R）-苯基甘氨醇对非手性或外消旋的芳基-δ-含氧酸进行脱水环化反应，立体选择性地得到手性非外消旋的双环内酰胺，由此对映异构体合成了（R）-和（S）-2-苯基哌啶，非对映异构体合成了顺式和反式-3-乙基-2-苯基哌啶，对映异构体合成了哌啶生物碱（-）-假木贼碱。
Cyclodehydration of achiral or racemic aryl-delta-oxoacids with (R)-phenylglycinol stereoselectively affords chiral non-racemic bicyclic lactams, from which the enantiodivergent synthesis of (R)- and (S)-2-phenylpiperidine, the diastereodivergent synthesis of cis- and trans-3-ethyl-2-phenylpiperidine, and the enantioselective synthesis of the piperidine alkaloid (-)-anabasine is reported.