Carbene-catalyzed enantioselective hydrophosphination of α-bromoenals to prepare phosphine-containing chiral molecules

Carbene-catalyzed enantioselective hydrophosphination of α-bromoenals to prepare phosphine-containing chiral molecules

Disclosed herein is the first carbene-organocatalyzed asymmetric addition of phosphine nucleophiles to the in situ generated α,β-unsaturated acyl azolium intermediates. Our reaction enantioselectively constructs carbon-phosphine bonds and prepares chiral phosphines with high optical purities. The ph...

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Bibliographic Details
Main Authors: Maiti, Rakesh, Yan, Jia-Lei, Yang, Xing, Mondal, Bivas, Xu, Jun, Chai, Huifang, Jin, Zhichao, Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2022
Subjects:
Science::Chemistry
Asymmetric Hydrophosphination
Chiral Phosphine
Online Access:https://hdl.handle.net/10356/155058
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Institution: Nanyang Technological University
Language: English
Description
Summary:Disclosed herein is the first carbene-organocatalyzed asymmetric addition of phosphine nucleophiles to the in situ generated α,β-unsaturated acyl azolium intermediates. Our reaction enantioselectively constructs carbon-phosphine bonds and prepares chiral phosphines with high optical purities. The phosphine products are suitable for transforming to chiral ligands or catalysts with applications in asymmetric catalysis. The diarylalkyl or trialkyl phosphine products from our catalytic reactions, air-sensitive and reactive in nature, can be trapped (and stored) in their sulfur-oxidized form for operational simplicities.

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