Stereodivergent diversity oriented synthesis of piperidine alkaloids

被引：24

作者：

Adriaenssens, Louis V. ^{[1
]}

Austin, Carolyn A.

Gibson, Mairi

Smith, David

Hartley, Richard C.

机构：

[1] Univ Glasgow, Dept Chem, WestCHEM, Glasgow G12 8QQ, Lanark, Scotland

[2] Sanofi Aventis, Alnwick Res Ctr, Alnwick NE66 2JH, Northd, England

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 22期

关键词：

amines; asymmetric synthesis; combinatorial chemistry; solid-phase synthesis; titanium complexes;

D O I：

10.1002/ejoc.200600744

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkylidenetitanium. reagents enable the reagent-controlled high throughput asymmetric synthesis of 2-substituted piperidines and rapid access to multiple cyclic imines using solid phase synthesis (SPS). The Schrock carbenes, generated by reduction of thioacetals, convert resin-bound esters into enol ethers. Treatment with acid releases amino ketones that are cyclized with TMSCI to give iminium salts. Reduction introduces a chiral centre at C-2, whose absolute stereochernistry is determined by a phenethylamine (PEA) chiral auxiliary. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).

引用

页码：4998 / 5001

页数：4

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