Aminomethylhydroxylation of alkenes: exploitation in the synthesis of scaffolds for small molecule libraries

Ignacio Colomer; Ololade Adeniji; George M. Burslem; Philip Craven; Martin Ohsten Rasmussen; Anthony Willaume; Tuomo Kalliokoski; Richard Foster; Stephen P. Marsden; Adam Nelson

doi:10.1016/j.bmc.2015.01.058

Aminomethylhydroxylation of alkenes: exploitation in the synthesis of scaffolds for small molecule libraries

Ignacio Colomer, Ololade Adeniji, George M. Burslem, Philip Craven, Martin Ohsten Rasmussen, Anthony Willaume, Tuomo Kalliokoski, Richard Foster, Stephen P. Marsden, Adam Nelson

Chemistry

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

10 Citations (Scopus)

Abstract

The application of [4+2] cycloadditions between alkenes and an N-benzoyl iminium species, generated in situ under acidic conditions, is described in the synthesis of diverse molecular scaffolds. The key reaction led to the formation of cyclic imidates in good yield and with high regioselectivity. It was demonstrated that the cyclic imidates may be readily converted into 1,3-amino alcohols. Incorporation of orthogonally-reactive functionality, such as aryl and alkyl bromides, into the cycloaddition substrates enabled the synthesis of additional scaffolds. For one scaffold, the synthesis of exemplar screening compounds was undertaken to demonstrate potential value in small molecule library production.

Original language	English
Pages (from-to)	2736-2740
Number of pages	5
Journal	Bioorganic & Medicinal Chemistry
Volume	23
Issue number	11
Early online date	10 Feb 2015
DOIs	https://doi.org/10.1016/j.bmc.2015.01.058
Publication status	Published - 1 Jun 2015

Keywords

Small molecule libraries
Cycloaddition
1,3-Amino alcohols

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Colomer, I., Adeniji, O., Burslem, G. M., Craven, P., Rasmussen, M. O., Willaume, A., Kalliokoski, T., Foster, R., Marsden, S. P., & Nelson, A. (2015). Aminomethylhydroxylation of alkenes: exploitation in the synthesis of scaffolds for small molecule libraries. Bioorganic & Medicinal Chemistry, 23(11), 2736-2740. Advance online publication. https://doi.org/10.1016/j.bmc.2015.01.058

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abstract = "The application of [4+2] cycloadditions between alkenes and an N-benzoyl iminium species, generated in situ under acidic conditions, is described in the synthesis of diverse molecular scaffolds. The key reaction led to the formation of cyclic imidates in good yield and with high regioselectivity. It was demonstrated that the cyclic imidates may be readily converted into 1,3-amino alcohols. Incorporation of orthogonally-reactive functionality, such as aryl and alkyl bromides, into the cycloaddition substrates enabled the synthesis of additional scaffolds. For one scaffold, the synthesis of exemplar screening compounds was undertaken to demonstrate potential value in small molecule library production.",

keywords = "Small molecule libraries, Cycloaddition, 1,3-Amino alcohols",

author = "Ignacio Colomer and Ololade Adeniji and Burslem, {George M.} and Philip Craven and Rasmussen, {Martin Ohsten} and Anthony Willaume and Tuomo Kalliokoski and Richard Foster and Marsden, {Stephen P.} and Adam Nelson",

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doi = "10.1016/j.bmc.2015.01.058",

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T1 - Aminomethylhydroxylation of alkenes

T2 - exploitation in the synthesis of scaffolds for small molecule libraries

AU - Colomer, Ignacio

AU - Adeniji, Ololade

AU - Burslem, George M.

AU - Craven, Philip

AU - Rasmussen, Martin Ohsten

AU - Willaume, Anthony

AU - Kalliokoski, Tuomo

AU - Foster, Richard

AU - Marsden, Stephen P.

AU - Nelson, Adam

PY - 2015/6/1

Y1 - 2015/6/1

N2 - The application of [4+2] cycloadditions between alkenes and an N-benzoyl iminium species, generated in situ under acidic conditions, is described in the synthesis of diverse molecular scaffolds. The key reaction led to the formation of cyclic imidates in good yield and with high regioselectivity. It was demonstrated that the cyclic imidates may be readily converted into 1,3-amino alcohols. Incorporation of orthogonally-reactive functionality, such as aryl and alkyl bromides, into the cycloaddition substrates enabled the synthesis of additional scaffolds. For one scaffold, the synthesis of exemplar screening compounds was undertaken to demonstrate potential value in small molecule library production.

AB - The application of [4+2] cycloadditions between alkenes and an N-benzoyl iminium species, generated in situ under acidic conditions, is described in the synthesis of diverse molecular scaffolds. The key reaction led to the formation of cyclic imidates in good yield and with high regioselectivity. It was demonstrated that the cyclic imidates may be readily converted into 1,3-amino alcohols. Incorporation of orthogonally-reactive functionality, such as aryl and alkyl bromides, into the cycloaddition substrates enabled the synthesis of additional scaffolds. For one scaffold, the synthesis of exemplar screening compounds was undertaken to demonstrate potential value in small molecule library production.

KW - Small molecule libraries

KW - Cycloaddition

KW - 1,3-Amino alcohols

UR - http://linkinghub.elsevier.com/retrieve/pii/S0968089615000826

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DO - 10.1016/j.bmc.2015.01.058

M3 - Article

SN - 0968-0896

VL - 23

SP - 2736

EP - 2740

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

IS - 11

ER -

Aminomethylhydroxylation of alkenes: exploitation in the synthesis of scaffolds for small molecule libraries

Abstract

Keywords

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