Asymmetric permanganate dihydroxylation of enoates: substrate scope, mechanistic insights and application in bicalutamide synthesis-Reference-Cited by-同舟云学术

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Asymmetric permanganate dihydroxylation of enoates: substrate scope, mechanistic insights and application in bicalutamide synthesis

Published:2024 Issue:3 Volume:11 Page:836-842
ISSN:2052-4129
Container-title:Organic Chemistry Frontiers
language:en
Short-container-title:Org. Chem. Front.

Author:

Gu Peilong¹,Wang Shuangshuang¹,Wen Xiangxiang¹,Tian Jinxin²,Wang Chao¹^ORCID,Zong Lili²^ORCID,Tan Choon-Hong³^ORCID

Affiliation:

1. Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China

2. School of Pharmaceutical Sciences, Xiamen University, Xiamen 361102, China

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

Abstract

Chiral cinchoninium catalysed permanganate dihydroxylation of enoates with different substitution types, including challenging tetrasubstituted ones, provides good yields of chiral vicinal diols in up to 98% ee.

Funder

Nanjing Tech University

National Natural Science Foundation of China

Natural Science Foundation of Jiangsu Province

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2024/QO/D3QO01729J

Reference56 articles.

1. Applications of sharpless asymmetric dihydroxylation in the total synthesis of natural products

2. Catalytic Asymmetric Dihydroxylation

3. Catalytic Epoxidation and syn-Dihydroxylation Reactions in Steroid Chemistry

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