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

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

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. © 2007 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	8550-8553
Number of pages	3
Journal	Tetrahedron Letters
Volume	48
Issue number	48
DOIs	https://doi.org/10.1016/j.tetlet.2007.09.150
Publication status	Published - 26 Nov 2007

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10.1016/j.tetlet.2007.09.150

CCDC 658994: Experimental Crystal Structure Determination
Clayden, J. (Contributor), Hebditch, K. R. (Contributor), Read, B. (Contributor) & Helliwell, M. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2008
DOI: 10.5517/ccq3qwd, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccq3qwd&sid=DataCite
Dataset
CCDC 658993: Experimental Crystal Structure Determination
Clayden, J. (Contributor), Hebditch, K. R. (Contributor), Read, B. (Contributor) & Helliwell, M. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2008
DOI: 10.5517/ccq3qvc, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccq3qvc&sid=DataCite
Dataset
CCDC 658992: Experimental Crystal Structure Determination
Clayden, J. (Contributor), Hebditch, K. R. (Contributor), Read, B. (Contributor) & Helliwell, M. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2007
DOI: 10.5517/ccq3qtb, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccq3qtb&sid=DataCite
Dataset

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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. {\textcopyright} 2007 Elsevier Ltd. All rights reserved.",

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

year = "2007",

month = nov,

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

language = "English",

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journal = "Tetrahedron Letters",

issn = "1873-3581",

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T1 - Oxidative fragmentation of bicyclic hydroxy silanes and stannanes: 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. © 2007 Elsevier Ltd. All rights reserved.

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. © 2007 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tetlet.2007.09.150

DO - 10.1016/j.tetlet.2007.09.150

M3 - Article

SN - 1873-3581

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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Datasets

CCDC 658994: Experimental Crystal Structure Determination

CCDC 658993: Experimental Crystal Structure Determination

CCDC 658992: Experimental Crystal Structure Determination

Cite this