Indium- and zinc-mediated Barbier-type allylations of an N,N-(dimethylsulfamoyl)-protected aldimine and subsequent deprotection

Sara Källström; Tiina Saloranta; Adriaan J. Minnaard; Reko Leino

doi:10.1016/j.tetlet.2007.07.167

Indium- and zinc-mediated Barbier-type allylations of an N,N-(dimethylsulfamoyl)-protected aldimine and subsequent deprotection

Sara Källström, Tiina Saloranta, Adriaan J. Minnaard, Reko Leino

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

19 Citations (Scopus)

Abstract

Barbier-type Zn and In-mediated allylations of an N,N-(dimethylsulfamoyl)-protected aldimine with different allyl bromides were investigated for the preparation of N-homoallylic sulfamides. The desired N,N-(dimethylsulfamoyl)-protected products were obtained in moderate to high yields in THF as the optimal solvent. Their further derivatization was demonstrated by a facile preparation of a functionalized dehydropiperidine by an allylation/olefin metathesis reaction sequence. A high yielding deprotection of the N,N-dimethylsulfamoyl group was likewise demonstrated. (c) 2007 Elsevier Ltd. All rights reserved.

Original language	Undefined/Unknown
Pages (from-to)	6958–6961
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	39
DOIs	https://doi.org/10.1016/j.tetlet.2007.07.167
Publication status	Published - 2007
MoE publication type	A1 Journal article-refereed

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10.1016/j.tetlet.2007.07.167

Cite this

@article{607a647b11ce489297580c71d96e2dc6,

title = "Indium- and zinc-mediated Barbier-type allylations of an N,N-(dimethylsulfamoyl)-protected aldimine and subsequent deprotection",

abstract = "Barbier-type Zn and In-mediated allylations of an N,N-(dimethylsulfamoyl)-protected aldimine with different allyl bromides were investigated for the preparation of N-homoallylic sulfamides. The desired N,N-(dimethylsulfamoyl)-protected products were obtained in moderate to high yields in THF as the optimal solvent. Their further derivatization was demonstrated by a facile preparation of a functionalized dehydropiperidine by an allylation/olefin metathesis reaction sequence. A high yielding deprotection of the N,N-dimethylsulfamoyl group was likewise demonstrated. (c) 2007 Elsevier Ltd. All rights reserved.",

author = "Sara K{\"a}llstr{\"o}m and Tiina Saloranta and Minnaard, {Adriaan J.} and Reko Leino",

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journal = "Tetrahedron Letters",

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T1 - Indium- and zinc-mediated Barbier-type allylations of an N,N-(dimethylsulfamoyl)-protected aldimine and subsequent deprotection

AU - Källström, Sara

AU - Saloranta, Tiina

AU - Minnaard, Adriaan J.

AU - Leino, Reko

PY - 2007

Y1 - 2007

N2 - Barbier-type Zn and In-mediated allylations of an N,N-(dimethylsulfamoyl)-protected aldimine with different allyl bromides were investigated for the preparation of N-homoallylic sulfamides. The desired N,N-(dimethylsulfamoyl)-protected products were obtained in moderate to high yields in THF as the optimal solvent. Their further derivatization was demonstrated by a facile preparation of a functionalized dehydropiperidine by an allylation/olefin metathesis reaction sequence. A high yielding deprotection of the N,N-dimethylsulfamoyl group was likewise demonstrated. (c) 2007 Elsevier Ltd. All rights reserved.

AB - Barbier-type Zn and In-mediated allylations of an N,N-(dimethylsulfamoyl)-protected aldimine with different allyl bromides were investigated for the preparation of N-homoallylic sulfamides. The desired N,N-(dimethylsulfamoyl)-protected products were obtained in moderate to high yields in THF as the optimal solvent. Their further derivatization was demonstrated by a facile preparation of a functionalized dehydropiperidine by an allylation/olefin metathesis reaction sequence. A high yielding deprotection of the N,N-dimethylsulfamoyl group was likewise demonstrated. (c) 2007 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tetlet.2007.07.167

DO - 10.1016/j.tetlet.2007.07.167

M3 - Artikel

SN - 0040-4039

VL - 48

SP - 6958

EP - 6961

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 39

ER -