2,6-Disubstituted and 2,2,6-Trisubstituted Piperidines from Serine: Asymmetric Synthesis and Further Elaboration

被引：14
|
作者：
Acharya, Hukum P. [1 ]
Clive, Derrick L. J. [1 ]
机构：
[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 15期
基金：
加拿大自然科学与工程研究理事会;
关键词：
RING-CLOSING METATHESIS; CLAISEN REARRANGEMENT; DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; QUINOLIZIDINE ALKALOIDS; EFFICIENT; INDOLIZIDINE; PYRROLIDINE; CYCLIZATION; ACETALS;
D O I：
10.1021/jo101010c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
4-Hydroxy-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl esters, which are readily prepared from serine and terminal acetylenes, undergo Claisen rearrangement to piperidine derivatives when heated with butyl vinyl ether in the presence of Hg(OAc)(2) and Et(3)N. This route to optically pure piperidines having substituents alpha to nitrogen is general, and the rearrangement products are versatile intermediates for making a broad range of amines containing a substituted piperidine subunit.
引用
收藏
页码：5223 / 5233
页数：11
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