Vinyl radical cyclization onto imino group. Selective 6-endo cyclization onto aldimines leading to 3-methylenepiperidines

Ilhyong Ryu; Shin ichi Ogura; Satoshi Minakata; Mitsuo Komatsu

doi:10.1016/S0040-4039(98)02666-5

Vinyl radical cyclization onto imino group. Selective 6-endo cyclization onto aldimines leading to 3-methylenepiperidines

Ilhyong Ryu^*, Shin ichi Ogura, Satoshi Minakata, Mitsuo Komatsu

^*Corresponding author for this work

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

37 Scopus citations

Abstract

When 5-exo/6-endo type of vinyl radical cyclization onto aldimine N=C bond was examined using tin hydride mediated radical reaction conditions, selective 6-endo cyclization took place to lead to 3-methylenepiperidines. On the other hand, vinyl radical cyclization onto ketimine N=C bond did not take place.

Original language	English
Pages (from-to)	1515-1518
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	8
DOIs	https://doi.org/10.1016/S0040-4039(98)02666-5
State	Published - 19 Feb 1999

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title = "Vinyl radical cyclization onto imino group. Selective 6-endo cyclization onto aldimines leading to 3-methylenepiperidines",

abstract = "When 5-exo/6-endo type of vinyl radical cyclization onto aldimine N=C bond was examined using tin hydride mediated radical reaction conditions, selective 6-endo cyclization took place to lead to 3-methylenepiperidines. On the other hand, vinyl radical cyclization onto ketimine N=C bond did not take place.",

author = "Ilhyong Ryu and Ogura, {Shin ichi} and Satoshi Minakata and Mitsuo Komatsu",

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T1 - Vinyl radical cyclization onto imino group. Selective 6-endo cyclization onto aldimines leading to 3-methylenepiperidines

AU - Ryu, Ilhyong

AU - Ogura, Shin ichi

AU - Minakata, Satoshi

AU - Komatsu, Mitsuo

PY - 1999/2/19

Y1 - 1999/2/19

N2 - When 5-exo/6-endo type of vinyl radical cyclization onto aldimine N=C bond was examined using tin hydride mediated radical reaction conditions, selective 6-endo cyclization took place to lead to 3-methylenepiperidines. On the other hand, vinyl radical cyclization onto ketimine N=C bond did not take place.

AB - When 5-exo/6-endo type of vinyl radical cyclization onto aldimine N=C bond was examined using tin hydride mediated radical reaction conditions, selective 6-endo cyclization took place to lead to 3-methylenepiperidines. On the other hand, vinyl radical cyclization onto ketimine N=C bond did not take place.

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U2 - 10.1016/S0040-4039(98)02666-5

DO - 10.1016/S0040-4039(98)02666-5

M3 - Article

AN - SCOPUS:0033582589

VL - 40

SP - 1515

EP - 1518

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 8

ER -

Vinyl radical cyclization onto imino group. Selective 6-endo cyclization onto aldimines leading to 3-methylenepiperidines

Abstract

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