Solid phase approaches to N-heterocycles using a sulfur linker cleaved by SmI2

Laura A. McAllister; Kristy L. Turner; Stephen Brand; Mark Stefaniak; David J. Procter

doi:10.1021/jo060940n

Solid phase approaches to N-heterocycles using a sulfur linker cleaved by SmI2

Laura A. McAllister, Kristy L. Turner, Stephen Brand, Mark Stefaniak, David J. Procter

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

Abstract

A sulfur HASC (α-hetero-atom substituted carbonyl) linker has been utilized in solid-phase approaches to oxindoles and tetrahydroquinolones. The route to oxindoles employs the first Pummerer cyclizations on solid phase, whereas the route to tetrahydroquinolones involves a microwave-assisted Heck reaction followed by a Michael cyclization. In both cases, the linker is cleaved in a traceless fashion by electron transfer from samarium(II) iodide. The routes illustrate the compatibility of the linker system with a number of reaction types and its utility for library synthesis. © 2006 American Chemical Society.

Original language	English
Pages (from-to)	6497-6507
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	71
Issue number	17
DOIs	https://doi.org/10.1021/jo060940n
Publication status	Published - 18 Aug 2006

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10.1021/jo060940n

CCDC 601447: Experimental Crystal Structure Determination
McAllister, L. A. (Contributor), Turner, K. L. (Contributor), Brand, S. (Contributor), Stefaniak, M. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2006
DOI: 10.5517/ccn5vj5, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccn5vj5&sid=DataCite
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title = "Solid phase approaches to N-heterocycles using a sulfur linker cleaved by SmI2",

abstract = "A sulfur HASC (α-hetero-atom substituted carbonyl) linker has been utilized in solid-phase approaches to oxindoles and tetrahydroquinolones. The route to oxindoles employs the first Pummerer cyclizations on solid phase, whereas the route to tetrahydroquinolones involves a microwave-assisted Heck reaction followed by a Michael cyclization. In both cases, the linker is cleaved in a traceless fashion by electron transfer from samarium(II) iodide. The routes illustrate the compatibility of the linker system with a number of reaction types and its utility for library synthesis. {\textcopyright} 2006 American Chemical Society.",

author = "McAllister, {Laura A.} and Turner, {Kristy L.} and Stephen Brand and Mark Stefaniak and Procter, {David J.}",

year = "2006",

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doi = "10.1021/jo060940n",

language = "English",

volume = "71",

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journal = "Journal of Organic Chemistry",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - Solid phase approaches to N-heterocycles using a sulfur linker cleaved by SmI2

AU - McAllister, Laura A.

AU - Turner, Kristy L.

AU - Brand, Stephen

AU - Stefaniak, Mark

AU - Procter, David J.

PY - 2006/8/18

Y1 - 2006/8/18

N2 - A sulfur HASC (α-hetero-atom substituted carbonyl) linker has been utilized in solid-phase approaches to oxindoles and tetrahydroquinolones. The route to oxindoles employs the first Pummerer cyclizations on solid phase, whereas the route to tetrahydroquinolones involves a microwave-assisted Heck reaction followed by a Michael cyclization. In both cases, the linker is cleaved in a traceless fashion by electron transfer from samarium(II) iodide. The routes illustrate the compatibility of the linker system with a number of reaction types and its utility for library synthesis. © 2006 American Chemical Society.

AB - A sulfur HASC (α-hetero-atom substituted carbonyl) linker has been utilized in solid-phase approaches to oxindoles and tetrahydroquinolones. The route to oxindoles employs the first Pummerer cyclizations on solid phase, whereas the route to tetrahydroquinolones involves a microwave-assisted Heck reaction followed by a Michael cyclization. In both cases, the linker is cleaved in a traceless fashion by electron transfer from samarium(II) iodide. The routes illustrate the compatibility of the linker system with a number of reaction types and its utility for library synthesis. © 2006 American Chemical Society.

U2 - 10.1021/jo060940n

DO - 10.1021/jo060940n

M3 - Article

SN - 0022-3263

VL - 71

SP - 6497

EP - 6507

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

Solid phase approaches to N-heterocycles using a sulfur linker cleaved by SmI2

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CCDC 601447: Experimental Crystal Structure Determination

Cite this