Diastereo- and Enantioselective Access to Stereotriads through a Flexible Coupling of Substituted Aldehydes and Alkenes

Jing Li; Alexander Preinfalk; Nuno Maulide

doi:10.1002/anie.201900801

Diastereo- and Enantioselective Access to Stereotriads through a Flexible Coupling of Substituted Aldehydes and Alkenes

Jing Li, Alexander Preinfalk, Nuno Maulide

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

8 Citations (Scopus)

Abstract

A flexible redox-neutral coupling of aldehydes and alkenes enables rapid access to stereotriads starting from a single stereocenter with perfect levels of enantio- and diastereoselectivity under mild conditions. The versatility of the method is highlighted by the installation of heteroatoms along the tether, which enables a route to structurally diverse building blocks. The formal synthesis of (+)-neopeltolide further demonstrates the synthetic utility of this approach.

Original language	English
Pages (from-to)	5887-5890
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	18
DOIs	https://doi.org/10.1002/anie.201900801
Publication status	Published - 2019 Apr 23
Externally published	Yes

Keywords

Neopeltolide
aldehydes
alkenes
coupling reactions
redox-neutral reactions

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201900801

Cite this

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abstract = "A flexible redox-neutral coupling of aldehydes and alkenes enables rapid access to stereotriads starting from a single stereocenter with perfect levels of enantio- and diastereoselectivity under mild conditions. The versatility of the method is highlighted by the installation of heteroatoms along the tether, which enables a route to structurally diverse building blocks. The formal synthesis of (+)-neopeltolide further demonstrates the synthetic utility of this approach.",

keywords = "Neopeltolide, aldehydes, alkenes, coupling reactions, redox-neutral reactions",

author = "Jing Li and Alexander Preinfalk and Nuno Maulide",

note = "Funding Information: Generous support of our research programs by the University of Vienna is acknowledged. We are grateful for financial support of this research by the ERC (CoG VINCAT), the FWF (Project P30226) and the Austrian Academy of Sciences (DOC Fellowship to A.P.). The invaluable assistance of Ing. A. Roller (UVienna) for X-ray crystallographic determination is acknowledged. Publisher Copyright: {\textcopyright} 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.",

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doi = "10.1002/anie.201900801",

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AU - Preinfalk, Alexander

AU - Maulide, Nuno

N1 - Funding Information: Generous support of our research programs by the University of Vienna is acknowledged. We are grateful for financial support of this research by the ERC (CoG VINCAT), the FWF (Project P30226) and the Austrian Academy of Sciences (DOC Fellowship to A.P.). The invaluable assistance of Ing. A. Roller (UVienna) for X-ray crystallographic determination is acknowledged. Publisher Copyright: © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

PY - 2019/4/23

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N2 - A flexible redox-neutral coupling of aldehydes and alkenes enables rapid access to stereotriads starting from a single stereocenter with perfect levels of enantio- and diastereoselectivity under mild conditions. The versatility of the method is highlighted by the installation of heteroatoms along the tether, which enables a route to structurally diverse building blocks. The formal synthesis of (+)-neopeltolide further demonstrates the synthetic utility of this approach.

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KW - Neopeltolide

KW - aldehydes

KW - alkenes

KW - coupling reactions

KW - redox-neutral reactions

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Diastereo- and Enantioselective Access to Stereotriads through a Flexible Coupling of Substituted Aldehydes and Alkenes

Abstract

Keywords

ASJC Scopus subject areas

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