Carbene-catalyzed activation of C-Si bonds for chemo- and enantioselective cross Brook–Benzoin reaction

Carbene-catalyzed activation of C-Si bonds for chemo- and enantioselective cross Brook–Benzoin reaction

The first carbene-catalyzed asymmetric chemoselective cross silyl benzoin (Brook-Benzoin) reaction has been developed. Key steps of this reaction involve activation of the carbon-silicon bond of an acylsilane by a chiral N-heterocyclic carbene (NHC) catalyst to form a silyl acyl anion intermediate....

Full description

Saved in:
Bibliographic Details
Main Authors: Tang, Chenghao, Wang, Wei, Luo, Guoyong, Song, Chaoyang, Bao, Zhaowei, Li, Pei, Hao, Gefei, Chi, Robin Yonggui, Jin, Zhichao
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2022
Subjects:
Science::Chemistry
Acylsilanes
Benzoin Condensation
Online Access:https://hdl.handle.net/10356/163498
Tags: Add Tag
No Tags, Be the first to tag this record!
Institution: Nanyang Technological University
Language: English
Description
Summary:The first carbene-catalyzed asymmetric chemoselective cross silyl benzoin (Brook-Benzoin) reaction has been developed. Key steps of this reaction involve activation of the carbon-silicon bond of an acylsilane by a chiral N-heterocyclic carbene (NHC) catalyst to form a silyl acyl anion intermediate. These acyl anions then undergo an addition reaction with indole aldehydes in a highly chemo- and enantioselective manner to afford α-silyloxy ketones with excellent optical purities. The reaction mechanism of this cross Brook-Benzoin reaction was investigated through both experimental and computational methods. The chiral α-hydroxy ketone derivatives obtained by this approach show promising, agrochemically interesting activity against harmful plant bacteria.

Similar Items