Oxidative fragmentation of bicyclic hydroxy silanes and stannanes: a strategy for the stereoselective synthesis of kainoids

Jonathan Clayden; Katherine R. Hebditch; Benjamin Read; Madeleine Helliwell

doi:10.1016/j.tetlet.2007.09.150

Oxidative fragmentation of bicyclic hydroxy silanes and stannanes: a strategy for the stereoselective synthesis of kainoids

Jonathan Clayden^*
, Katherine R. Hebditch
, Benjamin Read
, Madeleine Helliwell

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

8 Citations (Scopus)

Abstract

The addition of tin or silicon nucleophiles to bicyclic enones generated by dearomatising cyclisation gives stannanes and silanes stereoselectively. These compounds may be fragmented under oxidative conditions to generate substituted pyrrolidines bearing C2 and C3 substituents closely related to those found in the kainoid series of cyclic amino acids.

Original language	English
Pages (from-to)	8550-8553
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	48
Early online date	29 Sept 2007
DOIs	https://doi.org/10.1016/j.tetlet.2007.09.150
Publication status	Published - 26 Nov 2007

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Organic & Biological

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title = "Oxidative fragmentation of bicyclic hydroxy silanes and stannanes: a strategy for the stereoselective synthesis of kainoids",

abstract = "The addition of tin or silicon nucleophiles to bicyclic enones generated by dearomatising cyclisation gives stannanes and silanes stereoselectively. These compounds may be fragmented under oxidative conditions to generate substituted pyrrolidines bearing C2 and C3 substituents closely related to those found in the kainoid series of cyclic amino acids.",

author = "Jonathan Clayden and Hebditch, \{Katherine R.\} and Benjamin Read and Madeleine Helliwell",

year = "2007",

month = nov,

day = "26",

doi = "10.1016/j.tetlet.2007.09.150",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Oxidative fragmentation of bicyclic hydroxy silanes and stannanes

T2 - a strategy for the stereoselective synthesis of kainoids

AU - Clayden, Jonathan

AU - Hebditch, Katherine R.

AU - Read, Benjamin

AU - Helliwell, Madeleine

PY - 2007/11/26

Y1 - 2007/11/26

N2 - The addition of tin or silicon nucleophiles to bicyclic enones generated by dearomatising cyclisation gives stannanes and silanes stereoselectively. These compounds may be fragmented under oxidative conditions to generate substituted pyrrolidines bearing C2 and C3 substituents closely related to those found in the kainoid series of cyclic amino acids.

AB - The addition of tin or silicon nucleophiles to bicyclic enones generated by dearomatising cyclisation gives stannanes and silanes stereoselectively. These compounds may be fragmented under oxidative conditions to generate substituted pyrrolidines bearing C2 and C3 substituents closely related to those found in the kainoid series of cyclic amino acids.

UR - https://www.scopus.com/pages/publications/35548962680

U2 - 10.1016/j.tetlet.2007.09.150

DO - 10.1016/j.tetlet.2007.09.150

M3 - Article (Academic Journal)

AN - SCOPUS:35548962680

SN - 0040-4039

VL - 48

SP - 8550

EP - 8553

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 48

ER -

Oxidative fragmentation of bicyclic hydroxy silanes and stannanes: a strategy for the stereoselective synthesis of kainoids

Abstract

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