Brønsted acid catalyzed enantioselective addition of hydrazones to 3-indolylmethanols

Steffen Mader; Modhu Sudan Maji; Iuliana Atodiresei; Magnus Rueping

doi:10.1039/d2qo00840h

Brønsted acid catalyzed enantioselective addition of hydrazones to 3-indolylmethanols

Steffen Mader, Modhu Sudan Maji, Iuliana Atodiresei, Magnus Rueping

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

1 Scopus citations

Abstract

The organocatalytic asymmetric addition of hydrazones to indole derivatives in the presence of chiral Brønsted acids is reported. A large variety of substrates are tolerated and the products are obtained in good yields and with excellent enantioselectivities. This metal-free reaction provides a convenient route to enantiopure β-substituted tryptophan derivatives in a concise fashion.

Original language	English (US)
Journal	Organic Chemistry Frontiers
DOIs	https://doi.org/10.1039/d2qo00840h
State	Published - Jul 15 2022

Bibliographical note

KAUST Repository Item: Exported on 2022-09-14
Acknowledgements: The authors acknowledge generous support by KAUST and S. M. thanks the DFG (Deutsche Forschungsgemeinschaft) for financial support through the International Research TrainingGroup SeleCa (IRTG 1628).

ASJC Scopus subject areas

Organic Chemistry

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10.1039/d2qo00840h

https://repository.kaust.edu.sa/bitstream/10754/679649/1/d2qo00840h.pdf

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title = "Br{\o}nsted acid catalyzed enantioselective addition of hydrazones to 3-indolylmethanols",

abstract = "The organocatalytic asymmetric addition of hydrazones to indole derivatives in the presence of chiral Br{\o}nsted acids is reported. A large variety of substrates are tolerated and the products are obtained in good yields and with excellent enantioselectivities. This metal-free reaction provides a convenient route to enantiopure β-substituted tryptophan derivatives in a concise fashion.",

author = "Steffen Mader and Maji, {Modhu Sudan} and Iuliana Atodiresei and Magnus Rueping",

note = "KAUST Repository Item: Exported on 2022-09-14 Acknowledgements: The authors acknowledge generous support by KAUST and S. M. thanks the DFG (Deutsche Forschungsgemeinschaft) for financial support through the International Research TrainingGroup SeleCa (IRTG 1628).",

year = "2022",

month = jul,

day = "15",

doi = "10.1039/d2qo00840h",

language = "English (US)",

journal = "Organic Chemistry Frontiers",

issn = "2052-4129",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Brønsted acid catalyzed enantioselective addition of hydrazones to 3-indolylmethanols

AU - Mader, Steffen

AU - Maji, Modhu Sudan

AU - Atodiresei, Iuliana

AU - Rueping, Magnus

N1 - KAUST Repository Item: Exported on 2022-09-14 Acknowledgements: The authors acknowledge generous support by KAUST and S. M. thanks the DFG (Deutsche Forschungsgemeinschaft) for financial support through the International Research TrainingGroup SeleCa (IRTG 1628).

PY - 2022/7/15

Y1 - 2022/7/15

N2 - The organocatalytic asymmetric addition of hydrazones to indole derivatives in the presence of chiral Brønsted acids is reported. A large variety of substrates are tolerated and the products are obtained in good yields and with excellent enantioselectivities. This metal-free reaction provides a convenient route to enantiopure β-substituted tryptophan derivatives in a concise fashion.

AB - The organocatalytic asymmetric addition of hydrazones to indole derivatives in the presence of chiral Brønsted acids is reported. A large variety of substrates are tolerated and the products are obtained in good yields and with excellent enantioselectivities. This metal-free reaction provides a convenient route to enantiopure β-substituted tryptophan derivatives in a concise fashion.

UR - http://hdl.handle.net/10754/679649

UR - http://xlink.rsc.org/?DOI=D2QO00840H

U2 - 10.1039/d2qo00840h

DO - 10.1039/d2qo00840h

M3 - Article

SN - 2052-4129

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

ER -

Brønsted acid catalyzed enantioselective addition of hydrazones to 3-indolylmethanols

Abstract

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