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Nickel-catalyzed asymmetric reductive cross-couplings with vinyl bromide electrophiles

Hofstra, Julie and Suzuki, Naoyuki and Poremba, Kelsey and Reisman, Sarah E. (2017) Nickel-catalyzed asymmetric reductive cross-couplings with vinyl bromide electrophiles. In: 253rd American Chemical Society National Meeting & Exposition, April 2-6, 2017, San Francisco, CA.

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Nickel-catalyzed reductive cross-coupling reactions allow for the use of bench-stable electrophiles as both cross-coupling partners. In an effort to broaden the range of viable substrates in asym. transformations, two new cross-coupling reactions using vinyl bromide electrophiles were developed. The cross-coupling of vinyl bromides with chlorobenzyl silanes in the presence of a chiral nickel bis(oxazoline) catalyst and stoichiometric manganese reductant delivers chiral allyl silane products with excellent enantioselectivity. These products are known to participate in diastereoselective allylation reactions that form addnl. stereocenters, building mol. complexity. Application of the same catalyst-ligand system to the cross-coupling of vinyl bromides with N-hydroxyphthalimide esters gives rise to chiral allylic stereocenters in the presence of tetrakis(dimethylamino)ethylene as a terminal org. reductant.

Item Type:Conference or Workshop Item (Paper)
Related URLs:
URLURL TypeDescription Website
Hofstra, Julie0000-0001-9558-4317
Poremba, Kelsey0000-0002-7446-257X
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2017 American Chemical Society.
Record Number:CaltechAUTHORS:20170503-104847932
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:77153
Deposited By: Tony Diaz
Deposited On:03 May 2017 18:08
Last Modified:03 Oct 2019 17:54

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