Rhodium(II)-catalyzed stereoselective synthesis of allylsilanes

David M. Guptill; Carolyn M. Cohen; Huw M.L. Davies

doi:10.1021/ol4028978

Rhodium(II)-catalyzed stereoselective synthesis of allylsilanes

David M. Guptill
, Carolyn M. Cohen
, Huw M.L. Davies

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

19 Scopus citations

Abstract

The rhodium-catalyzed decomposition of 2-(triisopropylsilyl)ethyl aryl- and vinyldiazoacetates results in the stereoselective formation of Z-allylsilanes. The transformation is considered to proceed by silyl-directed intramolecular C-H functionalization to form a β-lactone intermediate followed by a silyl-activated extrusion of carbon dioxide.

Original language	English (US)
Pages (from-to)	6120-6123
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	24
DOIs	https://doi.org/10.1021/ol4028978
State	Published - Dec 20 2013
Externally published	Yes

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10.1021/ol4028978

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title = "Rhodium(II)-catalyzed stereoselective synthesis of allylsilanes",

abstract = "The rhodium-catalyzed decomposition of 2-(triisopropylsilyl)ethyl aryl- and vinyldiazoacetates results in the stereoselective formation of Z-allylsilanes. The transformation is considered to proceed by silyl-directed intramolecular C-H functionalization to form a β-lactone intermediate followed by a silyl-activated extrusion of carbon dioxide.",

author = "Guptill, \{David M.\} and Cohen, \{Carolyn M.\} and Davies, \{Huw M.L.\}",

year = "2013",

month = dec,

day = "20",

doi = "10.1021/ol4028978",

language = "English (US)",

volume = "15",

pages = "6120--6123",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "24",

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TY - JOUR

T1 - Rhodium(II)-catalyzed stereoselective synthesis of allylsilanes

AU - Guptill, David M.

AU - Cohen, Carolyn M.

AU - Davies, Huw M.L.

PY - 2013/12/20

Y1 - 2013/12/20

N2 - The rhodium-catalyzed decomposition of 2-(triisopropylsilyl)ethyl aryl- and vinyldiazoacetates results in the stereoselective formation of Z-allylsilanes. The transformation is considered to proceed by silyl-directed intramolecular C-H functionalization to form a β-lactone intermediate followed by a silyl-activated extrusion of carbon dioxide.

AB - The rhodium-catalyzed decomposition of 2-(triisopropylsilyl)ethyl aryl- and vinyldiazoacetates results in the stereoselective formation of Z-allylsilanes. The transformation is considered to proceed by silyl-directed intramolecular C-H functionalization to form a β-lactone intermediate followed by a silyl-activated extrusion of carbon dioxide.

UR - https://www.scopus.com/pages/publications/84890901368

UR - https://www.scopus.com/pages/publications/84890901368#tab=citedBy

U2 - 10.1021/ol4028978

DO - 10.1021/ol4028978

M3 - Article

AN - SCOPUS:84890901368

SN - 1523-7060

VL - 15

SP - 6120

EP - 6123

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Rhodium(II)-catalyzed stereoselective synthesis of allylsilanes

Abstract

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