Asymmetric synthesis of tricyclic 6,5,5-fused polycycles by the desymmetric Pauson

Asymmetric synthesis of tricyclic 6,5,5-fused polycycles by the desymmetric Pauson–Khand reaction

Published:2022 Issue:6 Volume:9 Page:1680-1685
ISSN:2052-4129
Container-title:Organic Chemistry Frontiers
language:en
Short-container-title:Org. Chem. Front.

Author:

Teng Qi¹,Chen Dong¹,Tung Chen-Ho¹^ORCID,Xu Zhenghu¹²³^ORCID

Affiliation:

1. Key Lab of Colloid and Interface Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, No. 27 South Shanda Road, Jinan, Shandong 250100, China

2. State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, PR China

3. Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science, Westlake University, 18 Shilongshan Road, Hangzhou 310024, Zhejiang Province, China

Abstract

A new rhodium(I)–BINAP-catalyzed enantioselective desymmetric Pauson–Khand (PK) reaction of prochiral 1,6-enynes with CO has been developed. Diverse tricyclic 6,5,5-fused bowl type polycycles were synthesized in one step with a single diastereomer.

Funder

National Natural Science Foundation of China

Fundamental Research Fund of Shandong University

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2022/QO/D1QO01878G

Reference61 articles.

1. Asymmetric Total Synthesis of the Highly Strained 4β-Acetoxyprobotryane-9β,15α-diol

2. Enantiospecific Total Synthesis of the Highly Strained (−)-Presilphiperfolan-8-ol via a Pd-Catalyzed Tandem Cyclization