Evaluation of Amino Nitriles and an Amino Imidate as Organocatalysts in Aldol Reactions

Nikolaos Vagkidis; Alexander J. Brown; Paul A. Clarke

doi:10.1055/s-0039-1690150

Evaluation of Amino Nitriles and an Amino Imidate as Organocatalysts in Aldol Reactions

Nikolaos Vagkidis, Alexander J. Brown, Paul A. Clarke^*

^*Corresponding author for this work

Chemistry

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

Abstract

The efficiency of l -valine and l -proline nitriles and a tert -butylÂ- l -proline imidate as organocatalysts for the aldol reaction have been evaluated. l -Valine nitrile was found to be a syn -selective catalyst, while l -proline nitrile was found to be anti -selective, and gave products in modest to good enantioselectivities. tert -Butyl l -proline imidate was found to be a very efficient catalyst in terms of conversion of starting reagents to products, and gave good anti -selectivity. The enantioselectivity of the tert -butyl l -proline imidate was found to be good to excellent, with products being formed in up to 94% enantiomeric excess.

Original language	English
Article number	SS-2019-T0330-OP
Pages (from-to)	4106-4112
Number of pages	7
Journal	SYNTHESIS-STUTTGART
Volume	51
Issue number	21
DOIs	https://doi.org/10.1055/s-0039-1690150
Publication status	Published - 8 Aug 2019

Bibliographical note

© 2019. Thieme. All rights reserved. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

Keywords

asymmetric synthesis
organocatalysis
amino imidate
amino nitrile
aldol reaction

Access to Document

10.1055/s-0039-1690150

Accepted Clarke imidate manuscript
© 2019. Thieme. All rights reserved
Accepted author manuscript, 1.82 MB

https://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0039-1690150.pdf

Cite this

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title = "Evaluation of Amino Nitriles and an Amino Imidate as Organocatalysts in Aldol Reactions",

abstract = "The efficiency of l -valine and l -proline nitriles and a tert -butyl{\^A}- l -proline imidate as organocatalysts for the aldol reaction have been evaluated. l -Valine nitrile was found to be a syn -selective catalyst, while l -proline nitrile was found to be anti -selective, and gave products in modest to good enantioselectivities. tert -Butyl l -proline imidate was found to be a very efficient catalyst in terms of conversion of starting reagents to products, and gave good anti -selectivity. The enantioselectivity of the tert -butyl l -proline imidate was found to be good to excellent, with products being formed in up to 94% enantiomeric excess.",

keywords = "asymmetric synthesis, organocatalysis, amino imidate, amino nitrile, aldol reaction",

author = "Nikolaos Vagkidis and Brown, {Alexander J.} and Clarke, {Paul A.}",

note = "{\textcopyright} 2019. Thieme. All rights reserved. This is an author-produced version of the published paper. Uploaded in accordance with the publisher{\textquoteright}s self-archiving policy. Further copying may not be permitted; contact the publisher for details. ",

year = "2019",

month = aug,

day = "8",

doi = "10.1055/s-0039-1690150",

language = "English",

volume = "51",

pages = "4106--4112",

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T1 - Evaluation of Amino Nitriles and an Amino Imidate as Organocatalysts in Aldol Reactions

AU - Vagkidis, Nikolaos

AU - Brown, Alexander J.

AU - Clarke, Paul A.

N1 - © 2019. Thieme. All rights reserved. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

PY - 2019/8/8

Y1 - 2019/8/8

N2 - The efficiency of l -valine and l -proline nitriles and a tert -butylÂ- l -proline imidate as organocatalysts for the aldol reaction have been evaluated. l -Valine nitrile was found to be a syn -selective catalyst, while l -proline nitrile was found to be anti -selective, and gave products in modest to good enantioselectivities. tert -Butyl l -proline imidate was found to be a very efficient catalyst in terms of conversion of starting reagents to products, and gave good anti -selectivity. The enantioselectivity of the tert -butyl l -proline imidate was found to be good to excellent, with products being formed in up to 94% enantiomeric excess.

AB - The efficiency of l -valine and l -proline nitriles and a tert -butylÂ- l -proline imidate as organocatalysts for the aldol reaction have been evaluated. l -Valine nitrile was found to be a syn -selective catalyst, while l -proline nitrile was found to be anti -selective, and gave products in modest to good enantioselectivities. tert -Butyl l -proline imidate was found to be a very efficient catalyst in terms of conversion of starting reagents to products, and gave good anti -selectivity. The enantioselectivity of the tert -butyl l -proline imidate was found to be good to excellent, with products being formed in up to 94% enantiomeric excess.

KW - asymmetric synthesis

KW - organocatalysis

KW - amino imidate

KW - amino nitrile

KW - aldol reaction

UR - http://www.scopus.com/inward/record.url?scp=85073712027&partnerID=8YFLogxK

U2 - 10.1055/s-0039-1690150

DO - 10.1055/s-0039-1690150

M3 - Article

AN - SCOPUS:85073712027

SN - 0039-7881

VL - 51

SP - 4106

EP - 4112

JO - SYNTHESIS-STUTTGART

JF - SYNTHESIS-STUTTGART

IS - 21

M1 - SS-2019-T0330-OP

ER -

Evaluation of Amino Nitriles and an Amino Imidate as Organocatalysts in Aldol Reactions

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Investigating the use of Amino nitriles and Amino imidates as organocatalysts

"Protocell" Catalysed Prebiotic Chemistry

Aminoimidate Catalysed Michael Addition of Carbonyl Compounds to Nitroalkenes

Evaluation of Amino Nitriles and Amino Imidates as Organocatalysts in Aldol Reactions

Cite this

Evaluation of Amino Nitriles and an Amino Imidate as Organocatalysts in Aldol Reactions

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Projects

Investigating the use of Amino nitriles and Amino imidates as organocatalysts

"Protocell" Catalysed Prebiotic Chemistry

Datasets

Aminoimidate Catalysed Michael Addition of Carbonyl Compounds to Nitroalkenes

Evaluation of Amino Nitriles and Amino Imidates as Organocatalysts in Aldol Reactions

Cite this