Shell Cross-Linked Micelles as Nanoreactors for Enantioselective Three-Step Tandem Catalysis

Kuepfert, Michael; Cohen, Aaron E.; Cullen, Olivia; Weck, Marcus

doi:10.1002/chem.201804956

Title: Shell Cross-Linked Micelles as Nanoreactors for Enantioselective Three-Step Tandem Catalysis

Journal Article · 01 October 2018 · Chemistry - A European Journal

DOI: https://doi.org/10.1002/chem.201804956 · OSTI ID:1657174

Kuepfert, Michael ^[1]; Cohen, Aaron E. ^[2]; Cullen, Olivia ^[2];

^[2]

New York University, NY (United States); NYU
New York University, NY (United States)

We describe functionalized amphiphilic poly(2-oxazoline)-based triblock copolymers that assemble into shell cross-linked micelles (SCMs). These micelles permit for the site isolation of three incompatible catalysts through compartmentalization, thereby enabling three-step non-orthogonal tandem processes in one pot. In particular, the acid catalyzed ketal hydrolysis to prochiral ketones proceeds in the hydrophilic corona, followed by the Rh-catalyzed asymmetric transfer hydrogenation to enantio-enriched alcohols in the cross-linked shell, and nucleophilic base-catalyzed acylation in the hydrophobic core. The catalysts are positioned in close proximity on a single micelle support to take advantage of intramicellar substrate diffusion, yet are sufficiently spaced apart from each other in physically distinct microenvironments. These compartmentalized micelles are substrate selective and, on a basic level, mimic compartmentalized catalytic architectures found in nature.

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Research Organization:: Georgia Institute of Technology, Atlanta, GA (United States)

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

Contributing Organization:: New York University

Grant/Contract Number:: FG02-03ER15459

OSTI ID:: 1657174

Journal Information:: Chemistry - A European Journal, Journal Name: Chemistry - A European Journal Journal Issue: 70 Vol. 24; ISSN 0947-6539

Publisher:: ChemPubSoc EuropeCopyright Statement

Country of Publication:: United States

Language:: English

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