Novel DMAP-catalyzed skeletal rearrangement of 5-exo-(2-hydroxyethylene)oxasilacyclopentanes

Dominique Bonafoux; Iwao Ojima

doi:10.1021/ol016153o

Novel DMAP-catalyzed skeletal rearrangement of 5-exo-(2-hydroxyethylene)oxasilacyclopentanes

Dominique Bonafoux
, Iwao Ojima

Chemistry

Stony Brook University

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

7 Scopus citations

Abstract

(matrix presented) 5-exo-(Hydroxyethylene)-2-oxa-1-silacyclopentanes are found to undergo a novel DMAP-catalyzed skeletal rearrangement through silicon -oxygen exchange during acetylation to yield the corresponding 5-(2-acetoxyalkyl)-2-oxa-1-silacyclopent-4-enes exclusively. The mechanism for this unprecedented rearrangement is proposed.

Original language	English
Pages (from-to)	2333-2335
Number of pages	3
Journal	Organic Letters
Volume	3
Issue number	15
DOIs	https://doi.org/10.1021/ol016153o
State	Published - Jul 26 2001

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@article{7d207043649e42b5bcd788bd18b4d355,

title = "Novel DMAP-catalyzed skeletal rearrangement of 5-exo-(2-hydroxyethylene)oxasilacyclopentanes",

abstract = "(matrix presented) 5-exo-(Hydroxyethylene)-2-oxa-1-silacyclopentanes are found to undergo a novel DMAP-catalyzed skeletal rearrangement through silicon -oxygen exchange during acetylation to yield the corresponding 5-(2-acetoxyalkyl)-2-oxa-1-silacyclopent-4-enes exclusively. The mechanism for this unprecedented rearrangement is proposed.",

author = "Dominique Bonafoux and Iwao Ojima",

year = "2001",

month = jul,

day = "26",

doi = "10.1021/ol016153o",

language = "English",

volume = "3",

pages = "2333--2335",

journal = "Organic Letters",

issn = "1523-7060",

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TY - JOUR

T1 - Novel DMAP-catalyzed skeletal rearrangement of 5-exo-(2-hydroxyethylene)oxasilacyclopentanes

AU - Bonafoux, Dominique

AU - Ojima, Iwao

PY - 2001/7/26

Y1 - 2001/7/26

N2 - (matrix presented) 5-exo-(Hydroxyethylene)-2-oxa-1-silacyclopentanes are found to undergo a novel DMAP-catalyzed skeletal rearrangement through silicon -oxygen exchange during acetylation to yield the corresponding 5-(2-acetoxyalkyl)-2-oxa-1-silacyclopent-4-enes exclusively. The mechanism for this unprecedented rearrangement is proposed.

AB - (matrix presented) 5-exo-(Hydroxyethylene)-2-oxa-1-silacyclopentanes are found to undergo a novel DMAP-catalyzed skeletal rearrangement through silicon -oxygen exchange during acetylation to yield the corresponding 5-(2-acetoxyalkyl)-2-oxa-1-silacyclopent-4-enes exclusively. The mechanism for this unprecedented rearrangement is proposed.

UR - https://www.scopus.com/pages/publications/0035954887

U2 - 10.1021/ol016153o

DO - 10.1021/ol016153o

M3 - Article

C2 - 11463309

AN - SCOPUS:0035954887

SN - 1523-7060

VL - 3

SP - 2333

EP - 2335

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Novel DMAP-catalyzed skeletal rearrangement of 5-exo-(2-hydroxyethylene)oxasilacyclopentanes

Abstract

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