Catalytic Asymmetric Cycloaddition of Ketenes and Nitroso Compounds: Enantioselective Synthesis of α-Hydroxycarboxylic Acid Derivatives

Dochnahl, Maximilian and Fu, Gregory C. (2009) Catalytic Asymmetric Cycloaddition of Ketenes and Nitroso Compounds: Enantioselective Synthesis of α-Hydroxycarboxylic Acid Derivatives. Angewandte Chemie International Edition, 48 (13). pp. 2391-2393. ISSN 1433-7851. PMCID PMC2728616. doi:10.1002/anie.200805805. https://resolver.caltech.edu/CaltechAUTHORS:20200518-080028686

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Abstract

The appropriate choice of chiral catalyst and starting materials leads to the synthesis of 1,2‐oxazetidin‐3‐ones by cycloadditions of ketenes with nitroso compounds with very good regioselectivity and enantioselectivity. In addition to serving as potentially bioactive target molecules, the products can be transformed into other important classes of compounds, such as α‐hydroxycarboxylic acid derivatives.

Item Type:

Article

Related URLs:

URL	URL Type	Description
https://doi.org/10.1002/anie.200805805	DOI	Article
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2728616	PubMed Central	Article

ORCID:

Author	ORCID
Fu, Gregory C.	0000-0002-0927-680X

Additional Information:

© 2009 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. Received: November 28, 2008; Published online: February 16, 2009. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, grant R01-GM57034), the German Academic Exchange Service (postdoctoral fellowship for M.D.), Merck Research Laboratories, and Novartis.

Funders:

Funding Agency	Grant Number
NIH	R01-GM57034
Deutscher Akademischer Austauschdienst (DAAD)	UNSPECIFIED
Merck Research Laboratories	UNSPECIFIED
Novartis	UNSPECIFIED

Subject Keywords:

asymmetric catalysis; carboxylic acids; cycloaddition; heterocycles; ketenes

Issue or Number:

PubMed Central ID:

PMC2728616

DOI:

10.1002/anie.200805805

Record Number:

CaltechAUTHORS:20200518-080028686

Persistent URL:

https://resolver.caltech.edu/CaltechAUTHORS:20200518-080028686

Official Citation:

Dochnahl, M. and Fu, G. (2009), Catalytic Asymmetric Cycloaddition of Ketenes and Nitroso Compounds: Enantioselective Synthesis of α‐Hydroxycarboxylic Acid Derivatives. Angewandte Chemie International Edition, 48: 2391-2393. doi:10.1002/anie.200805805

Usage Policy:

No commercial reproduction, distribution, display or performance rights in this work are provided.

ID Code:

103260

Collection:

CaltechAUTHORS

Deposited By:

Tony Diaz

Deposited On:

18 May 2020 15:29

Last Modified:

16 Nov 2021 18:19

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