C(6)-alkylation of 3-hydroxypiperidine via reductive and homolytic cleavage of N,S-Acetals

被引：9

作者：

Bartels, M ^{[1
]}

Zapico, J ^{[1
]}

Gallagher, T ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

来源：

SYNLETT | 2004年 / 14期

关键词：

piperidines; alkylation; anodic oxidation; radical;

D O I：

10.1055/s-2004-832846

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Carboxymethyl 3-hydroxypiperidine (6) undergoes substitution at C(6) via reductive cleavage of N,S-acetal 8a with lithium naphthalenide (LN) and trapping of the resulting carbanionic intermediate 9 with different electrophiles to give adducts 10. N,S-Acetal 8a also undergoes C-S homolysis and trapping of the resulting radical provides an alternative entry to 2-substituted-5-hydroxypiperidines.

引用

页码：2636 / 2638

页数：3

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