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General combinatorial synthesis of tertiary amines on solid support. A novel conditional release strategy based on traceless linking at nitrogen

Gustafsson, Magnus LU ; Olsson, Roger LU and Andersson, Carl Magnus LU (2001) In Tetrahedron Letters 42(1). p.133-136
Abstract

A novel solid phase synthesis of tertiary amines involving iodide-induced cleavage of the N-O bond of resin bound alkoxyammonium intermediates is described. The quaternary intermediates were assembled via sequential reductive aminations followed by alkylation. Cleavage from the solid support was induced by iodide ion or base, to afford the target tertiary amines in excellent purity.

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author
; and
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Conditional release, LiI, N-O cleavage, SmI, Solid phase, Tertiary amines
in
Tetrahedron Letters
volume
42
issue
1
pages
133 - 136
publisher
Elsevier
external identifiers
  • scopus:0035180617
ISSN
0040-4039
DOI
10.1016/S0040-4039(00)01902-X
language
English
LU publication?
no
id
289b2647-afb0-4cbb-b1e8-4e968800485f
date added to LUP
2019-10-02 10:40:31
date last changed
2020-01-13 02:26:23
@article{289b2647-afb0-4cbb-b1e8-4e968800485f,
  abstract     = {<p>A novel solid phase synthesis of tertiary amines involving iodide-induced cleavage of the N-O bond of resin bound alkoxyammonium intermediates is described. The quaternary intermediates were assembled via sequential reductive aminations followed by alkylation. Cleavage from the solid support was induced by iodide ion or base, to afford the target tertiary amines in excellent purity.</p>},
  author       = {Gustafsson, Magnus and Olsson, Roger and Andersson, Carl Magnus},
  issn         = {0040-4039},
  language     = {eng},
  month        = {01},
  number       = {1},
  pages        = {133--136},
  publisher    = {Elsevier},
  series       = {Tetrahedron Letters},
  title        = {General combinatorial synthesis of tertiary amines on solid support. A novel conditional release strategy based on traceless linking at nitrogen},
  url          = {http://dx.doi.org/10.1016/S0040-4039(00)01902-X},
  doi          = {10.1016/S0040-4039(00)01902-X},
  volume       = {42},
  year         = {2001},
}