A Nanovessel-Catalyzed Three-Component Aza-Darzens Reaction

Bierschenk, Stephen M.; Bergman, Robert G.; Raymond, Kenneth N.; Toste, F. Dean

doi:10.1021/jacs.9b13177

Title: A Nanovessel-Catalyzed Three-Component Aza-Darzens Reaction

Journal Article · 06 January 2020 · Journal of the American Chemical Society

DOI: https://doi.org/10.1021/jacs.9b13177 · OSTI ID:1633257

Bierschenk, Stephen M. ^[1]; Bergman, Robert G. ^[1];

^[1];

^[1]

Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Univ. of California, Berkeley, CA (United States)

It has been previously demonstrated that nanovessels can be highly competent catalysts providing high rate accelerations and unique selectivity to the organic transformations which they mediate. However, for supramolecular assemblies to be considered a standard reagent in organic synthesis they must first demonstrate the ability to catalyze increasingly complex transformations. Here in this paper, we report a three-component Aza-Darzens reaction that generates N-phenylaziridines, catalyzed by a supramolecular host, that provides the stereoisomer opposite to the one generated in bulk solution (trans vs cis). This transformation constitutes a rare catalytic three-component coupling within a supramolecular assembly, providing a supramolecular solution to a synthetically challenging transformation.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1633257

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 2 Vol. 142; ISSN 0002-7863; ISSN 1520-5126

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited By (3)

Substrate and product binding inside a stimuli-responsive coordination cage acting as a singlet oxygen photosensitizer Pullen, Sonja; Löffler, Susanne; Platzek, André Dalton Transactions, Vol. 49, Issue 27 https://doi.org/10.1039/d0dt01674h	journal	January 2020
Preparation of cage-shaped hexakis(spiroborate)s Danjo, Hiroshi; Masuda, Yuhki; Kidena, Yuki Organic & Biomolecular Chemistry, Vol. 18, Issue 19 https://doi.org/10.1039/d0ob00518e	journal	January 2020
Substrate and product binding inside a stimuli-responsive coordination cage acting as singlet oxygen photosensitizer Pullen, Sonja; Löffler, Susanne; Platzek, André Technische Universität Dortmund https://doi.org/10.17877/de290r-21187	text	January 2020

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