Cyclopropanespiro-?-lactones derived from 4-[(Z)-ethylidene]-3- methyloxetan-2-one: Diastereoselective formation and rearrangement reactions: Diastereoselective formation and rearrangement reactions

Patrick Mcardle; Niall W.A. Geraghty

doi:10.1016/j.tet.2011.03.013

Cyclopropanespiro-?-lactones derived from 4-[(Z)-ethylidene]-3- methyloxetan-2-one: Diastereoselective formation and rearrangement reactions: Diastereoselective formation and rearrangement reactions

Patrick Mcardle
, Niall W.A. Geraghty

Cellular & Molecular Medicine

University of Galway

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

7 Citations (Scopus)

Abstract

The metal catalysed reaction of monosubstituted diazo esters and ketones with 4-[(Z)-ethylidene]-3-methyloxetan-2-one results in the formation of cyclopropanespiro-beta-lactones. In contrast to most alkene cyclopropanations, including those involving diketene, the reaction occurs diastereoselectively. A computational model of the reaction has been developed that accounts for the observed stereochemistry. The metal promoted thermal rearrangement of these spiro compounds is also unusual in that it affords pyranones, rather than the decarboxylation products characteristic of beta-lactones in general, or the furanones formed from diketene derived cyclopropanespiro-il-lactones. (c) 2011 Elsevier Ltd. All rights reserved.

Original language	English (Ireland)
Pages (from-to)	3546-3552
Number of pages	7
Journal	Tetrahedron
Volume	67
Issue number	19
DOIs	https://doi.org/10.1016/j.tet.2011.03.013
Publication status	Published - 1 Jan 2011

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Authors
Geraghty,N.W.A.,McArdle, P.,Mullen,L.M.A.
Geraghty, NWA,McArdle, P,Mullen, LMA

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10.1016/j.tet.2011.03.013

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title = "Cyclopropanespiro-?-lactones derived from 4-[(Z)-ethylidene]-3- methyloxetan-2-one: Diastereoselective formation and rearrangement reactions: Diastereoselective formation and rearrangement reactions",

abstract = "The metal catalysed reaction of monosubstituted diazo esters and ketones with 4-[(Z)-ethylidene]-3-methyloxetan-2-one results in the formation of cyclopropanespiro-beta-lactones. In contrast to most alkene cyclopropanations, including those involving diketene, the reaction occurs diastereoselectively. A computational model of the reaction has been developed that accounts for the observed stereochemistry. The metal promoted thermal rearrangement of these spiro compounds is also unusual in that it affords pyranones, rather than the decarboxylation products characteristic of beta-lactones in general, or the furanones formed from diketene derived cyclopropanespiro-il-lactones. (c) 2011 Elsevier Ltd. All rights reserved.",

author = "Patrick Mcardle and Geraghty, \{Niall W.A.\}",

year = "2011",

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doi = "10.1016/j.tet.2011.03.013",

language = "English (Ireland)",

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Cyclopropanespiro-?-lactones derived from 4-[(Z)-ethylidene]-3- methyloxetan-2-one: Diastereoselective formation and rearrangement reactions: Diastereoselective formation and rearrangement reactions. / Mcardle, Patrick; Geraghty, Niall W.A.
In: Tetrahedron, Vol. 67, No. 19, 01.01.2011, p. 3546-3552.

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

TY - JOUR

T1 - Cyclopropanespiro-?-lactones derived from 4-[(Z)-ethylidene]-3- methyloxetan-2-one: Diastereoselective formation and rearrangement reactions

T2 - Diastereoselective formation and rearrangement reactions

AU - Mcardle, Patrick

AU - Geraghty, Niall W.A.

PY - 2011/1/1

Y1 - 2011/1/1

N2 - The metal catalysed reaction of monosubstituted diazo esters and ketones with 4-[(Z)-ethylidene]-3-methyloxetan-2-one results in the formation of cyclopropanespiro-beta-lactones. In contrast to most alkene cyclopropanations, including those involving diketene, the reaction occurs diastereoselectively. A computational model of the reaction has been developed that accounts for the observed stereochemistry. The metal promoted thermal rearrangement of these spiro compounds is also unusual in that it affords pyranones, rather than the decarboxylation products characteristic of beta-lactones in general, or the furanones formed from diketene derived cyclopropanespiro-il-lactones. (c) 2011 Elsevier Ltd. All rights reserved.

AB - The metal catalysed reaction of monosubstituted diazo esters and ketones with 4-[(Z)-ethylidene]-3-methyloxetan-2-one results in the formation of cyclopropanespiro-beta-lactones. In contrast to most alkene cyclopropanations, including those involving diketene, the reaction occurs diastereoselectively. A computational model of the reaction has been developed that accounts for the observed stereochemistry. The metal promoted thermal rearrangement of these spiro compounds is also unusual in that it affords pyranones, rather than the decarboxylation products characteristic of beta-lactones in general, or the furanones formed from diketene derived cyclopropanespiro-il-lactones. (c) 2011 Elsevier Ltd. All rights reserved.

UR - https://www.scopus.com/pages/publications/79954990665

U2 - 10.1016/j.tet.2011.03.013

DO - 10.1016/j.tet.2011.03.013

M3 - Article

VL - 67

SP - 3546

EP - 3552

JO - Tetrahedron

JF - Tetrahedron

IS - 19

ER -

Cyclopropanespiro-?-lactones derived from 4-[(Z)-ethylidene]-3- methyloxetan-2-one: Diastereoselective formation and rearrangement reactions: Diastereoselective formation and rearrangement reactions

Abstract

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