Synthesis of Enantiopure Dehydropiperidinones from α-Amino Acids and Alkynes via Azetidin-3-ones

Ishida, Naoki; Yuhki, Tatsuya; Murakami, Masahiro

doi:10.1021/ol3016447

Cited by 50 publications

(9 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Related 3-oxetanone-based processes were also disclosed. This report was followed quickly by similar studies from Kumar and Louie and Murakami and co-workers, with the latter focusing on 2-substituted 3-azetidinones. In these cases, β-carbon elimination was selective for the less hindered C–C bond and complete retention of C2 stereochemistry was observed.…”

Section: β-Carbon Elimination-based Methodologiesmentioning

confidence: 70%

Recent Methodologies That Exploit C–C Single-Bond Cleavage of Strained Ring Systems by Transition Metal Complexes

2017

View full text Add to dashboard Cite

show abstract

Section: β-Carbon Elimination-based Methodologiesmentioning

confidence: 70%

Recent Methodologies That Exploit C–C Single-Bond Cleavage of Strained Ring Systems by Transition Metal Complexes

2017

View full text Add to dashboard Cite

show abstract

“…15 This could allow a rather direct and efficient access to a broad range of 2,3-disubstituted azetidines, 16 and other pharmaceutically relevant nitrogen heterocycles. 17 Our proposed strategy from commercial N-Boc-azetidin-3-one is depicted in Scheme 1. The α-lithiation and alkylation of selected N-protected azetidines is well documented, providing further encouragement for this study.…”

Section: Figure 1 Examples Of Biologically Active 3-oxygenated Azetimentioning

confidence: 99%

Asymmetric Synthesis of 2-Substituted Azetidin-3-ones via Metalated SAMP/RAMP Hydrazones

et al. 2016

View full text Add to dashboard Cite

Permanent WRAP URL:http://wrap.warwick.ac.uk/79725 Copyright and reuse:The Warwick Research Archive Portal (WRAP) makes this work by researchers of the University of Warwick available open access under the following conditions. Copyright © and all moral rights to the version of the paper presented here belong to the individual author(s) and/or other copyright owners. To the extent reasonable and practicable the material made available in WRAP has been checked for eligibility before being made available.Copies of full items can be used for personal research or study, educational, or not-for profit purposes without prior permission or charge. Provided that the authors, title and full bibliographic details are credited, a hyperlink and/or URL is given for the original metadata page and the content is not changed in any way. Publisher's statement:"This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Journal of Organic Chemistry copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work http://pubs.acs.org/page/policy/articlesonrequest/index.html ." A note on versions:The version presented here may differ from the published version or, version of record, if you wish to cite this item you are advised to consult the publisher's version. Please see the 'permanent WRAP url' above for details on accessing the published version and note that access may require a subscription. Just Accepted "Just Accepted" manuscripts have been peer-reviewed and accepted for publication. They are posted online prior to technical editing, formatting for publication and author proofing. The American Chemical Society provides "Just Accepted" as a free service to the research community to expedite the dissemination of scientific material as soon as possible after acceptance. "Just Accepted" manuscripts appear in full in PDF format accompanied by an HTML abstract. "Just Accepted" manuscripts have been fully peer reviewed, but should not be considered the official version of record. They are accessible to all readers and citable by the Digital Object Identifier (DOI®). "Just Accepted" is an optional service offered to authors. Therefore, the "Just Accepted" Web site may not include all articles that will be published in the journal. After a manuscript is technically edited and formatted, it will be removed from the "Just Accepted" Web site and published as an ASAP article. Note that technical editing may introduce minor changes to the manuscript text and/or graphics which could affect content, and all legal disclaimers and ethical guidelines that apply to the journal pertain. ACS cannot be held responsible for errors or consequences arising from the use of information contained in these "Just Accepted" manuscripts. Asymmetric Synthesis of 2-Substituted Azetidin-3-ones via Metalated SAMP/RAMP Hydrazones TABLE OF CONTENTS/ABSTRACT:2-Substituted azetidin-3-ones can be prepared in good yields and enantioselectivities ...

show abstract

“…Metal-catalyzed cycloadditions based on the insertion of p-unsaturated reactants into activated C-C bonds now represent a broad area of research (1)(2)(3)(4). Intermolecular cycloadditions of cyclobutanone derivatives, which are catalyzed by nickel (11,(18)(19)(20)(21)(22)(23), rhodium (24,25), and ruthenium (24,26) complexes, constitute a growing subset of these transformations. To our knowledge, the formal insertion of saturated C-H bonds into C-C s bonds has not been documented.…”

mentioning

confidence: 99%

Ruthenium-catalyzed insertion of adjacent diol carbon atoms into C-C bonds: Entry to type II polyketides

Bender

Turnbull

Ambler

et al. 2017

Science

View full text Add to dashboard Cite

Current catalytic processes involving C-C bond activation rely on π-unsaturated coupling partners. Exploiting the concept of transfer hydrogenative coupling, we report here a ruthenium(0)-catalyzed cycloaddition of benzocyclobutenones that functionalizes two adjacent saturated diol C-H bonds. These regio- and diastereoselective processes enable convergent construction of type II polyketide substructures.

show abstract

Synthesis of Enantiopure Dehydropiperidinones from α-Amino Acids and Alkynes via Azetidin-3-ones

Abstract: Chiral dehydropiperidinones were synthesized in enantiopure form from α-amino acids and alkynes via azetidin-3-ones.

Cited by 50 publications

References 45 publications

Recent Methodologies That Exploit C–C Single-Bond Cleavage of Strained Ring Systems by Transition Metal Complexes

Recent Methodologies That Exploit C–C Single-Bond Cleavage of Strained Ring Systems by Transition Metal Complexes

Asymmetric Synthesis of 2-Substituted Azetidin-3-ones via Metalated SAMP/RAMP Hydrazones

Ruthenium-catalyzed insertion of adjacent diol carbon atoms into C-C bonds: Entry to type II polyketides

Contact Info

Product

Resources

About