Bisguanidinium-catalyzed formation of oxygen-containing quaternary stereogenic carbon centers-Reference-Cited by-同舟云学术

Bisguanidinium-catalyzed formation of oxygen-containing quaternary stereogenic carbon centers

Published:2023 Issue:21 Volume:10 Page:5416-5420
ISSN:2052-4129
Container-title:Organic Chemistry Frontiers
language:en
Short-container-title:Org. Chem. Front.

Author:

Ban Xu¹,Chen Changxing²,Khoa Kha Tuan³^ORCID,Wang Chao²^ORCID,Jiang Zhiyong¹,Tan Choon-Hong¹³^ORCID

Affiliation:

1. School of Chemistry and Chemical Engineering Henan Normal University; Pingyuan Laboratory, Xinxiang, Henan, 453007, P. R. China

2. Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing, 211816, P. R. China

3. School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore

Abstract

A bisguanidinium-catalyzed enantioconvergent SN2X reaction is described for the formation of C(sp3)–O bonds from racemic tertiary bromides and hydroxylamides/phenols, enabling efficient synthesis of bioactive compounds such as enantiopure bicalutamide and chiral fibrates.

Funder

National Natural Science Foundation of China

Nanjing Tech University

Natural Science Foundation of Jiangsu Province

Nanyang Technological University

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2023/QO/D3QO01332D

Reference39 articles.

1. Asymmetric Synthesis of Tertiary Alcohols and α-Tertiary Amines via Cu-Catalyzed C−C Bond Formation to Ketones and Ketimines

2. Recent Advances in Catalytic Asymmetric Synthesis of Tertiary Alcohols via Nucleophilic Addition to Ketones

3. Asymmetric catalysis for the construction of quaternary carbon centres: nucleophilic addition on ketones and ketimines

4. Catalytic Enantioselective Addition of Allylic Organometallic Reagents to Aldehydes and Ketones

5. Catalytic Enantioselective Allylation of Carbonyl Compounds and Imines

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