Diastereoselective [2,3]-Sigmatropic Rearrangement of N-Allyl Ammonium Ylides

Aleksandra Murre; Kristin Erkman; Sandra Kaabel; Ivar Järving; Tõnis Kanger

doi:10.1055/s-0039-1690185

Diastereoselective [2,3]-Sigmatropic Rearrangement of N-Allyl Ammonium Ylides

Aleksandra Murre, Kristin Erkman, Sandra Kaabel, Ivar Järving, Tõnis Kanger^*

^*Corresponding author for this work

Not published at Aalto University

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

3 Citations (Scopus)

Abstract

A rapid and diastereoselective method was developed for the [2,3]-sigmatropic rearrangement of N-Allyl ammonium ylides, affording products in up to 95% isolated yields and up to 97:3 dr; most of the desired products were formed within 1 minute. For the asymmetric reaction, a chiral auxiliary was introduced to the starting compound, affording the rearrangement product with high diastereoselectivities.

Original language	English
Pages (from-to)	4183-4197
Number of pages	15
Journal	Synthesis (Germany)
Volume	51
Issue number	22
DOIs	https://doi.org/10.1055/s-0039-1690185
Publication status	Published - 2019
MoE publication type	A1 Journal article-refereed

Keywords

ammonium ylide
auxiliary
diastereoselectivity
oxazolidinyl group
[2,3]-sigmatropic rearrangement
α-Amino ketones

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title = "Diastereoselective [2,3]-Sigmatropic Rearrangement of N-Allyl Ammonium Ylides",

abstract = "A rapid and diastereoselective method was developed for the [2,3]-sigmatropic rearrangement of N-Allyl ammonium ylides, affording products in up to 95% isolated yields and up to 97:3 dr; most of the desired products were formed within 1 minute. For the asymmetric reaction, a chiral auxiliary was introduced to the starting compound, affording the rearrangement product with high diastereoselectivities.",

keywords = "ammonium ylide, auxiliary, diastereoselectivity, oxazolidinyl group, [2,3]-sigmatropic rearrangement, α-Amino ketones",

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T1 - Diastereoselective [2,3]-Sigmatropic Rearrangement of N-Allyl Ammonium Ylides

AU - Murre, Aleksandra

AU - Erkman, Kristin

AU - Kaabel, Sandra

AU - Järving, Ivar

AU - Kanger, Tõnis

PY - 2019

Y1 - 2019

N2 - A rapid and diastereoselective method was developed for the [2,3]-sigmatropic rearrangement of N-Allyl ammonium ylides, affording products in up to 95% isolated yields and up to 97:3 dr; most of the desired products were formed within 1 minute. For the asymmetric reaction, a chiral auxiliary was introduced to the starting compound, affording the rearrangement product with high diastereoselectivities.

AB - A rapid and diastereoselective method was developed for the [2,3]-sigmatropic rearrangement of N-Allyl ammonium ylides, affording products in up to 95% isolated yields and up to 97:3 dr; most of the desired products were formed within 1 minute. For the asymmetric reaction, a chiral auxiliary was introduced to the starting compound, affording the rearrangement product with high diastereoselectivities.

KW - ammonium ylide

KW - auxiliary

KW - diastereoselectivity

KW - oxazolidinyl group

KW - [2,3]-sigmatropic rearrangement

KW - α-Amino ketones

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U2 - 10.1055/s-0039-1690185

DO - 10.1055/s-0039-1690185

M3 - Article

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VL - 51

SP - 4183

EP - 4197

JO - SYNTHESIS: STUTTGART

JF - SYNTHESIS: STUTTGART

SN - 0039-7881

IS - 22

ER -

Diastereoselective [2,3]-Sigmatropic Rearrangement of N-Allyl Ammonium Ylides

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Keywords

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