Stereodivergent Csp³-Csp³ bond construction via Lewis base/iridium cooperative catalysis: a modular synthesis of tertiary fluoride-containing stereodiads.
- 1Indiana University, Department of Chemistry 800 E. Kirkwood Ave. Bloomington IN 47405 USA [email protected] https://snaddon.lab.indiana.edu.
Abstract
The synthesis of tertiary fluoride-containing stereogenic centers remains a significant challenge. This challenge is amplified when such units are embedded within vicinal stereocenters arrays, where both absolute and relative stereochemistry must be controlled. Here we disclose a stereodivergent Lewis base-iridium cooperative catalysis method that unites α-fluorinated C1-ammonium enolate and π(allyl)Ir intermediates to construct tertiary fluoride-containing stereodiads. Each catalyst is independently responsible for the configurational outcome of each stereocenter comprising the stereodiad during Csp³-Csp³ bond construction. The conversion of easily prepared racemic α-fluoro esters to single α-fluoro C1-ammonium enolates via Lewis base catalysis is noteworthy.
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BibTeX
@article{mandal2026stereodivergent,
title = {{Stereodivergent Csp³-Csp³ bond construction via Lewis base/iridium cooperative catalysis: a modular synthesis of tertiary fluoride-containing stereodiads.}},
author = {Smita Mandal and Maren Pink and Thomas N Snaddon},
journal = {Chemical science},
year = {2026},
month = oct,
doi = {10.1039/d6sc06429a},
url = {https://europepmc.org/article/MED/42909855},
note = {CC BY},
}
RIS
TY - JOUR
TI - Stereodivergent Csp³-Csp³ bond construction via Lewis base/iridium cooperative catalysis: a modular synthesis of tertiary fluoride-containing stereodiads.
AU - Smita Mandal
AU - Maren Pink
AU - Thomas N Snaddon
PY - 2026
DA - 2026/10/21
JO - Chemical science
DO - 10.1039/d6sc06429a
UR - https://europepmc.org/article/MED/42909855
AB - The synthesis of tertiary fluoride-containing stereogenic centers remains a significant challenge. This challenge is amplified when such units are embedded within vicinal stereocenters arrays, where both absolute and relative stereochemistry must be controlled. Here we disclose a stereodivergent Lewis base-iridium cooperative catalysis method that unites α-fluorinated C1-ammonium enolate and π(allyl)Ir intermediates to construct tertiary fluoride-containing stereodiads. Each catalyst is independently responsible for the configurational outcome of each stereocenter comprising the stereodiad during Csp³-Csp³ bond construction. The conversion of easily prepared racemic α-fluoro esters to single α-fluoro C1-ammonium enolates via Lewis base catalysis is noteworthy.
SN - 2041-6520
SN - 2041-6539
ER -