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

Forskningsoutput: Tidskriftsbidrag › Artikel › Vetenskaplig › Peer review

20 Citeringar (Scopus)

Sammanfattning

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.

Originalspråk	Odefinierat/okänt
Sidor (från-till)	6958–6961
Antal sidor	4
Tidskrift	Tetrahedron Letters
Volym	48
Nummer	39
DOI	https://doi.org/10.1016/j.tetlet.2007.07.167
Status	Publicerad - 2007
MoE-publikationstyp	A1 Tidskriftsartikel-refererad

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10.1016/j.tetlet.2007.07.167

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@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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language = "Odefinierat/ok{\"a}nt",

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TY - JOUR

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 -