Samarium(II)-mediated reactions of γ,δ-unsaturated ketones. Cyclization and fragmentation processes

Thomas K. Hutton; Kenneth Muir; David J. Procter

doi:10.1021/ol0260472

Samarium(II)-mediated reactions of γ,δ-unsaturated ketones. Cyclization and fragmentation processes

Thomas K. Hutton, Kenneth Muir, David J. Procter

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Abstract

(Matrix Presented) On treatment with samarium(II) iodide, γ,δ-unsaturated ketones undergo very different processes depending upon the nature of the reaction conditions. Employing samarium(II) iodide and MeOH, functionalized syn-cyclopentanol products are obtained stereoselectively. Mechanistic studies suggest that this cyclization occurs via a sequential reduction/intramolecular aldol reaction. With samarium(II) iodide and HMPA, products of a 4-exo-trig cyclization and of an interesting fragmentation reaction are observed.

Original language	English
Pages (from-to)	2345-2347
Number of pages	2
Journal	Organic Letters
Volume	4
Issue number	14
DOIs	https://doi.org/10.1021/ol0260472
Publication status	Published - 11 Jul 2002

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10.1021/ol0260472

CCDC 184372: Experimental Crystal Structure Determination
Hutton, T. K. (Contributor), Muir, K. W. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2002
DOI: 10.5517/cc65vhp, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc65vhp&sid=DataCite
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title = "Samarium(II)-mediated reactions of γ,δ-unsaturated ketones. Cyclization and fragmentation processes",

abstract = "(Matrix Presented) On treatment with samarium(II) iodide, γ,δ-unsaturated ketones undergo very different processes depending upon the nature of the reaction conditions. Employing samarium(II) iodide and MeOH, functionalized syn-cyclopentanol products are obtained stereoselectively. Mechanistic studies suggest that this cyclization occurs via a sequential reduction/intramolecular aldol reaction. With samarium(II) iodide and HMPA, products of a 4-exo-trig cyclization and of an interesting fragmentation reaction are observed.",

author = "Hutton, {Thomas K.} and Kenneth Muir and Procter, {David J.}",

year = "2002",

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T1 - Samarium(II)-mediated reactions of γ,δ-unsaturated ketones. Cyclization and fragmentation processes

AU - Hutton, Thomas K.

AU - Muir, Kenneth

AU - Procter, David J.

PY - 2002/7/11

Y1 - 2002/7/11

N2 - (Matrix Presented) On treatment with samarium(II) iodide, γ,δ-unsaturated ketones undergo very different processes depending upon the nature of the reaction conditions. Employing samarium(II) iodide and MeOH, functionalized syn-cyclopentanol products are obtained stereoselectively. Mechanistic studies suggest that this cyclization occurs via a sequential reduction/intramolecular aldol reaction. With samarium(II) iodide and HMPA, products of a 4-exo-trig cyclization and of an interesting fragmentation reaction are observed.

AB - (Matrix Presented) On treatment with samarium(II) iodide, γ,δ-unsaturated ketones undergo very different processes depending upon the nature of the reaction conditions. Employing samarium(II) iodide and MeOH, functionalized syn-cyclopentanol products are obtained stereoselectively. Mechanistic studies suggest that this cyclization occurs via a sequential reduction/intramolecular aldol reaction. With samarium(II) iodide and HMPA, products of a 4-exo-trig cyclization and of an interesting fragmentation reaction are observed.

U2 - 10.1021/ol0260472

DO - 10.1021/ol0260472

M3 - Article

VL - 4

SP - 2345

EP - 2347

JO - Organic Letters

JF - Organic Letters

SN - 1523-7052

IS - 14

ER -

Samarium(II)-mediated reactions of γ,δ-unsaturated ketones. Cyclization and fragmentation processes

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CCDC 184372: Experimental Crystal Structure Determination

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