PADAM reactions of α-aminoaldehydes: Identity of major and minor diastereomers from the Passerini reaction

Memory Zimuwandeyi; Fatima Kola; Andreas Lemmerer; Dean Brady; Amanda L. Rousseau; Moira L. Bode

doi:10.1016/j.tet.2018.04.065

PADAM reactions of α-aminoaldehydes: Identity of major and minor diastereomers from the Passerini reaction

Memory Zimuwandeyi, Fatima Kola, Andreas Lemmerer, Dean Brady, Amanda L. Rousseau, Moira L. Bode

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

6 Scopus citations

Abstract

The Passerini reaction was conducted using N-Boc-L-phenylalaninal and a variety of achiral or chiral acids and isocyanides to prepare a library of 27 Passerini products. Reaction diastereoselectivity varied between 1.7:1 and 2.5:1 and in most cases isolation of the individual diastereomers was possible. Passerini products were subjected to a deprotection and acyl migration sequence to give a library of peptidomimetic α-hydroxy-β-acylaminoamides in generally excellent yield. Single crystal X-ray analysis of two of the final products enabled identification of the major diastereomer as having an (R) configuration at the newly-formed stereogenic centre, which corresponds to anti-Felkin-Anh addition of the isocyanide to the aldehyde.

Original language	English
Pages (from-to)	2925-2941
Number of pages	17
Journal	Tetrahedron
Volume	74
Issue number	24
DOIs	https://doi.org/10.1016/j.tet.2018.04.065
State	Published - 14 Jun 2018
Externally published	Yes

Keywords

Diastereoselectivity
Major diastereomer
PADAM
Passerini
α-aminoaldehydes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2018.04.065

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title = "PADAM reactions of α-aminoaldehydes: Identity of major and minor diastereomers from the Passerini reaction",

abstract = "The Passerini reaction was conducted using N-Boc-L-phenylalaninal and a variety of achiral or chiral acids and isocyanides to prepare a library of 27 Passerini products. Reaction diastereoselectivity varied between 1.7:1 and 2.5:1 and in most cases isolation of the individual diastereomers was possible. Passerini products were subjected to a deprotection and acyl migration sequence to give a library of peptidomimetic α-hydroxy-β-acylaminoamides in generally excellent yield. Single crystal X-ray analysis of two of the final products enabled identification of the major diastereomer as having an (R) configuration at the newly-formed stereogenic centre, which corresponds to anti-Felkin-Anh addition of the isocyanide to the aldehyde.",

keywords = "Diastereoselectivity, Major diastereomer, PADAM, Passerini, α-aminoaldehydes",

author = "Memory Zimuwandeyi and Fatima Kola and Andreas Lemmerer and Dean Brady and Rousseau, {Amanda L.} and Bode, {Moira L.}",

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doi = "10.1016/j.tet.2018.04.065",

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T1 - PADAM reactions of α-aminoaldehydes

T2 - Identity of major and minor diastereomers from the Passerini reaction

AU - Zimuwandeyi, Memory

AU - Kola, Fatima

AU - Lemmerer, Andreas

AU - Brady, Dean

AU - Rousseau, Amanda L.

AU - Bode, Moira L.

PY - 2018/6/14

Y1 - 2018/6/14

N2 - The Passerini reaction was conducted using N-Boc-L-phenylalaninal and a variety of achiral or chiral acids and isocyanides to prepare a library of 27 Passerini products. Reaction diastereoselectivity varied between 1.7:1 and 2.5:1 and in most cases isolation of the individual diastereomers was possible. Passerini products were subjected to a deprotection and acyl migration sequence to give a library of peptidomimetic α-hydroxy-β-acylaminoamides in generally excellent yield. Single crystal X-ray analysis of two of the final products enabled identification of the major diastereomer as having an (R) configuration at the newly-formed stereogenic centre, which corresponds to anti-Felkin-Anh addition of the isocyanide to the aldehyde.

AB - The Passerini reaction was conducted using N-Boc-L-phenylalaninal and a variety of achiral or chiral acids and isocyanides to prepare a library of 27 Passerini products. Reaction diastereoselectivity varied between 1.7:1 and 2.5:1 and in most cases isolation of the individual diastereomers was possible. Passerini products were subjected to a deprotection and acyl migration sequence to give a library of peptidomimetic α-hydroxy-β-acylaminoamides in generally excellent yield. Single crystal X-ray analysis of two of the final products enabled identification of the major diastereomer as having an (R) configuration at the newly-formed stereogenic centre, which corresponds to anti-Felkin-Anh addition of the isocyanide to the aldehyde.

KW - Diastereoselectivity

KW - Major diastereomer

KW - PADAM

KW - Passerini

KW - α-aminoaldehydes

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DO - 10.1016/j.tet.2018.04.065

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SN - 0040-4020

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SP - 2925

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JO - Tetrahedron

JF - Tetrahedron

IS - 24

ER -

PADAM reactions of α-aminoaldehydes: Identity of major and minor diastereomers from the Passerini reaction

Abstract

Keywords

ASJC Scopus subject areas

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