Allylindium and allylboronic acid pinacolate: Mild reagents for the allylation of resin-bound aldehydes. Application to the solid-phase synthesis of hydroxypropylamines

Cullen L. Cavallaro; Timothy Herpin; Brian F. McGuinness; Yvonne Class Shimshock; Roland E. Dolle

doi:10.1016/S0040-4039(99)00346-9

Allylindium and allylboronic acid pinacolate: Mild reagents for the allylation of resin-bound aldehydes. Application to the solid-phase synthesis of hydroxypropylamines

Cullen L. Cavallaro, Timothy Herpin, Brian F. McGuinness, Yvonne Class Shimshock, Roland E. Dolle

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

13 Scopus citations

Abstract

Homoallylic alcohols are prepared in high yield and puritY by the reaction of the title reagents with resin-bound aldehydes. The mild reaction conditions accommodate the base-sensitive 4-carboxamido-3-nitrobenzyl photolabile linker on standard resins. A practical application of the allylation reaction is demonstrated through the solid-phase synthesis of hydroxypropylamines.

Original language	English
Pages (from-to)	2711-2714
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	14
DOIs	https://doi.org/10.1016/S0040-4039(99)00346-9
State	Published - Apr 2 1999

Keywords

Allylation
Homoallylic alcohol
Indium
Solid-phase synthesis, hydroxypropylamine

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10.1016/S0040-4039(99)00346-9

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title = "Allylindium and allylboronic acid pinacolate: Mild reagents for the allylation of resin-bound aldehydes. Application to the solid-phase synthesis of hydroxypropylamines",

abstract = "Homoallylic alcohols are prepared in high yield and puritY by the reaction of the title reagents with resin-bound aldehydes. The mild reaction conditions accommodate the base-sensitive 4-carboxamido-3-nitrobenzyl photolabile linker on standard resins. A practical application of the allylation reaction is demonstrated through the solid-phase synthesis of hydroxypropylamines.",

keywords = "Allylation, Homoallylic alcohol, Indium, Solid-phase synthesis, hydroxypropylamine",

author = "Cavallaro, {Cullen L.} and Timothy Herpin and McGuinness, {Brian F.} and Shimshock, {Yvonne Class} and Dolle, {Roland E.}",

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Allylindium and allylboronic acid pinacolate: Mild reagents for the allylation of resin-bound aldehydes. Application to the solid-phase synthesis of hydroxypropylamines. / Cavallaro, Cullen L.; Herpin, Timothy; McGuinness, Brian F. et al.
In: Tetrahedron Letters, Vol. 40, No. 14, 02.04.1999, p. 2711-2714.

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

TY - JOUR

T1 - Allylindium and allylboronic acid pinacolate

T2 - Mild reagents for the allylation of resin-bound aldehydes. Application to the solid-phase synthesis of hydroxypropylamines

AU - Cavallaro, Cullen L.

AU - Herpin, Timothy

AU - McGuinness, Brian F.

AU - Shimshock, Yvonne Class

AU - Dolle, Roland E.

PY - 1999/4/2

Y1 - 1999/4/2

N2 - Homoallylic alcohols are prepared in high yield and puritY by the reaction of the title reagents with resin-bound aldehydes. The mild reaction conditions accommodate the base-sensitive 4-carboxamido-3-nitrobenzyl photolabile linker on standard resins. A practical application of the allylation reaction is demonstrated through the solid-phase synthesis of hydroxypropylamines.

AB - Homoallylic alcohols are prepared in high yield and puritY by the reaction of the title reagents with resin-bound aldehydes. The mild reaction conditions accommodate the base-sensitive 4-carboxamido-3-nitrobenzyl photolabile linker on standard resins. A practical application of the allylation reaction is demonstrated through the solid-phase synthesis of hydroxypropylamines.

KW - Allylation

KW - Homoallylic alcohol

KW - Indium

KW - Solid-phase synthesis, hydroxypropylamine

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U2 - 10.1016/S0040-4039(99)00346-9

DO - 10.1016/S0040-4039(99)00346-9

M3 - Article

AN - SCOPUS:0033515857

SN - 0040-4039

VL - 40

SP - 2711

EP - 2714

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 14

ER -

Allylindium and allylboronic acid pinacolate: Mild reagents for the allylation of resin-bound aldehydes. Application to the solid-phase synthesis of hydroxypropylamines

Abstract

Keywords

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