Radical cyclisation of amino aldehydes leading to hydroxy pyrrolidines and piperidines

A F  Parsons; R M  Pettifer

Radical cyclisation of amino aldehydes leading to hydroxy pyrrolidines and piperidines

Chemistry

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

Abstract

The cyclisation of amino aldehydes using Bu3SnH in boiling benzene is reported. The reaction proceeds via addition of a tributyltin radical to the aldehyde forming an O-stannyl ketyl and radical cyclisation onto electron poor or rich double bonds gives rise to hydroxy pyrrolidines and piperidines. (C) 1997 Elsevier Science Ltd.

Original language	English
Pages (from-to)	5907-5910
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	33
Publication status	Published - 18 Aug 1997

Keywords

O-STANNYL KETYLS
MEDIATED RING-CLOSURE
SUBSTITUTED PYRROLIDINES
REDUCTIVE CYCLIZATION
KETONES
ALKENES

Cite this

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title = "Radical cyclisation of amino aldehydes leading to hydroxy pyrrolidines and piperidines",

abstract = "The cyclisation of amino aldehydes using Bu3SnH in boiling benzene is reported. The reaction proceeds via addition of a tributyltin radical to the aldehyde forming an O-stannyl ketyl and radical cyclisation onto electron poor or rich double bonds gives rise to hydroxy pyrrolidines and piperidines. (C) 1997 Elsevier Science Ltd.",

keywords = "O-STANNYL KETYLS, MEDIATED RING-CLOSURE, SUBSTITUTED PYRROLIDINES, REDUCTIVE CYCLIZATION, KETONES, ALKENES",

author = "Parsons, {A F} and Pettifer, {R M}",

year = "1997",

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language = "English",

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pages = "5907--5910",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Radical cyclisation of amino aldehydes leading to hydroxy pyrrolidines and piperidines

AU - Parsons, A F

AU - Pettifer, R M

PY - 1997/8/18

Y1 - 1997/8/18

N2 - The cyclisation of amino aldehydes using Bu3SnH in boiling benzene is reported. The reaction proceeds via addition of a tributyltin radical to the aldehyde forming an O-stannyl ketyl and radical cyclisation onto electron poor or rich double bonds gives rise to hydroxy pyrrolidines and piperidines. (C) 1997 Elsevier Science Ltd.

AB - The cyclisation of amino aldehydes using Bu3SnH in boiling benzene is reported. The reaction proceeds via addition of a tributyltin radical to the aldehyde forming an O-stannyl ketyl and radical cyclisation onto electron poor or rich double bonds gives rise to hydroxy pyrrolidines and piperidines. (C) 1997 Elsevier Science Ltd.

KW - O-STANNYL KETYLS

KW - MEDIATED RING-CLOSURE

KW - SUBSTITUTED PYRROLIDINES

KW - REDUCTIVE CYCLIZATION

KW - KETONES

KW - ALKENES

M3 - Article

SN - 0040-4039

VL - 38

SP - 5907

EP - 5910

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 33

ER -