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- Title
Contra‐Thermodynamic, Photocatalytic <italic>E</italic>→<italic>Z</italic> Isomerization of Styrenyl Boron Species: Vectors to Facilitate Exploration of Two‐Dimensional Chemical Space.
- Authors
Molloy, John J.; Metternich, Jan B.; Daniliuc, Constantin G.; Watson, Allan J. B.; Gilmour, Ryan
- Abstract
Abstract: Designing strategies to access stereodefined olefinic organoboron species is an important synthetic challenge. Despite significant advances, there is a striking paucity of routes to <italic>Z</italic>‐α‐substituted styrenyl organoborons. Herein, this strategic imbalance is redressed by exploiting the polarity of the C(sp2)−B bond to activate the neighboring π system, thus enabling a mild, traceless photocatalytic isomerization of readily accessible <italic>E</italic>‐α‐substituted styrenyl BPins to generate the corresponding <italic>Z</italic>‐isomers with high fidelity. Preliminary validation of this contra‐thermodynamic <italic>E</italic>→<italic>Z</italic> isomerization is demonstrated in a series of stereoretentive transformations to generate <italic>Z</italic>‐configured trisubstituted alkenes, as well as in a concise synthesis of the anti‐tumor agent Combretastatin A4.
- Subjects
UNITED States. Bureau of Reclamation; ISOMERIZATION; BORON; SPECIES
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 12, p3222
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201800286