Diastereo- and enantioselective synthesis of biaryl aldehydes bearing both axial and central chirality

Fen Huang; Ling-Fei Tao; Jiyong Liu; Linghui Qian; Jia-Yu Liao

doi:10.1039/D3CC00708A

Diastereo- and enantioselective synthesis of biaryl aldehydes bearing both axial and central chirality

Fen Huang
, Ling-Fei Tao
, Jiyong Liu
, Linghui Qian^*
, Jia-Yu Liao^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

22 Citations (Scopus)

Abstract

We describe herein an intriguing method for the synthesis of biaryl aldehydes bearing both axial and central chirality through a desymmetric [3 + 2] cycloaddition reaction of activated isocyanides with prochiral biaryl dialdehydes under silver catalysis. This protocol features excellent enantioselectivity, 100% atom economy, good functional group compatibility, and operational simplicity.

Original language	English
Pages (from-to)	4487-4490
Number of pages	4
Journal	Chemical Communications
Volume	59
Issue number	30
Early online date	21 Mar 2023
DOIs	https://doi.org/10.1039/D3CC00708A
Publication status	Published - 18 Apr 2023

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SDG 9 Industry, Innovation, and Infrastructure

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title = "Diastereo- and enantioselective synthesis of biaryl aldehydes bearing both axial and central chirality",

abstract = "We describe herein an intriguing method for the synthesis of biaryl aldehydes bearing both axial and central chirality through a desymmetric [3 + 2] cycloaddition reaction of activated isocyanides with prochiral biaryl dialdehydes under silver catalysis. This protocol features excellent enantioselectivity, 100\% atom economy, good functional group compatibility, and operational simplicity.",

author = "Fen Huang and Ling-Fei Tao and Jiyong Liu and Linghui Qian and Jia-Yu Liao",

note = "We are grateful for the financial support from the National Natural Science Foundation of China (82273887), and the Joint Funds of the Zhejiang Provincial Natural Science Foundation of China (LTZ22B020001). Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2023",

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T1 - Diastereo- and enantioselective synthesis of biaryl aldehydes bearing both axial and central chirality

AU - Huang, Fen

AU - Tao, Ling-Fei

AU - Liu, Jiyong

AU - Qian, Linghui

AU - Liao, Jia-Yu

N1 - We are grateful for the financial support from the National Natural Science Foundation of China (82273887), and the Joint Funds of the Zhejiang Provincial Natural Science Foundation of China (LTZ22B020001). Publisher Copyright: © The Royal Society of Chemistry 2023

PY - 2023/4/18

Y1 - 2023/4/18

N2 - We describe herein an intriguing method for the synthesis of biaryl aldehydes bearing both axial and central chirality through a desymmetric [3 + 2] cycloaddition reaction of activated isocyanides with prochiral biaryl dialdehydes under silver catalysis. This protocol features excellent enantioselectivity, 100% atom economy, good functional group compatibility, and operational simplicity.

AB - We describe herein an intriguing method for the synthesis of biaryl aldehydes bearing both axial and central chirality through a desymmetric [3 + 2] cycloaddition reaction of activated isocyanides with prochiral biaryl dialdehydes under silver catalysis. This protocol features excellent enantioselectivity, 100% atom economy, good functional group compatibility, and operational simplicity.

U2 - 10.1039/D3CC00708A

DO - 10.1039/D3CC00708A

M3 - Journal article

SN - 1359-7345

VL - 59

SP - 4487

EP - 4490

JO - Chemical Communications

JF - Chemical Communications

IS - 30

ER -

Diastereo- and enantioselective synthesis of biaryl aldehydes bearing both axial and central chirality

Abstract

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