Diethylaminosulfur Trifluoride (DAST)-Mediated Intramolecular Benzannulation of o-Allylchalcones: Synthesis of 3-Fluorotetralins-Reference-Cited by-同舟云学术

Diethylaminosulfur Trifluoride (DAST)-Mediated Intramolecular Benzannulation of o-Allylchalcones: Synthesis of 3-Fluorotetralins

Published:2019-04-01 Issue:12 Volume:51 Page:2553-2563
ISSN:0039-7881
Container-title:Synthesis
language:en
Short-container-title:Synthesis

Author:

Chang Meng-Yang¹²^ORCID,Chen Han-Yu¹,Tsai Yu-Lin¹

Affiliation:

1. Department of Medicinal and Applied Chemistry, Kaohsiung Medical University

2. Department of Medical Research, Kaohsiung Medical University Hospital

Abstract

A concise route for the synthesis of 3-fluorotetralines is described, including: (i) NaBH4-mediated reduction of oxygenated o-allylchalcones and (ii) sequential DAST-mediated intramolecular annulation of the resulting alkenols. A plausible mechanism is proposed and discussed. This protocol provides highly effective regio- and stereocontrolled allyl-enone cross-coupling to construct two stereocenters and one E-configured styryl group.

Funder

Ministry of Science and Technology, Taiwan

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0037-1612419.pdf

Cited by 5 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Oxidation and Reduction;Organic Reaction Mechanisms Series;2023-01-20

2. α,β-Unsaturated Carbonyls for One-Pot Transition-Metal-Free Access to 3,6-Dihydro-2H-pyrans;The Journal of Organic Chemistry;2022-05-17

3. Diethylaminosulfur Trifluoride (DAST) Mediated Transformations Leading to Valuable Building Blocks and Bioactive Compounds;European Journal of Organic Chemistry;2021-09-30

4. PdCl 2 /CuCl 2 /Bi(OTf) 3 ‐promoted Construction of Sulfonyl Dibenzooxabicyclo[3.3.1]nonanes and Arylnaphthalenes via Intramolecular Annulation of Sulfonyl o ‐Allylarylchromanones;Advanced Synthesis & Catalysis;2020-11-11

5. One‐Pot Access to Sulfonyl 2‐Arylnaphthalenes via Wacker Oxidation of Sulfonyl o ‐Allylchalcones;Advanced Synthesis & Catalysis;2020-09-17