Next Article in Journal
Synthesis of Meso-Diarylaminocorroles via SNAr Reactions
Previous Article in Journal
Intrinsic Flexibility of the EMT Zeolite Framework under Pressure
Article Menu
Issue 3 (February-1) cover image

Export Article

Open AccessCommunication
Molecules 2019, 24(3), 643; https://doi.org/10.3390/molecules24030643

Synthesis of a Conformationally Stable Atropisomeric Pair of Biphenyl Scaffold Containing Additional Stereogenic Centers

1
The Hong Kong Polytechnic University Shenzhen Research Institute, Shenzhen 518000, PR China
2
State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon 999077, Hong Kong
*
Author to whom correspondence should be addressed.
Received: 18 January 2019 / Revised: 6 February 2019 / Accepted: 8 February 2019 / Published: 12 February 2019
(This article belongs to the Section Organic Chemistry)
Full-Text   |   PDF [2465 KB, uploaded 12 February 2019]   |  

Abstract

The synthesis of a new CF3-containing stereogenic atropisomeric pair of ortho-disubstituted biphenyl scaffold is presented. The atropisomers are surprisingly conformationally stable for isolation. X-ray structures show that their stability comes from an intramolecular hydrogen bond formation from their two hydroxyl groups and renders the spatial arrangement of their peripheral CF3 and CH3 groups very different. The synthesized stereogenic scaffold proved to be effective in catalyzing the asymmetric N-nitroso aldol reaction of enamine and nitrosobenzene. Compared to similar scaffolds without CF3 groups, one of our atropisomer exhibits an increase in enantioselectivity in this reaction. View Full-Text
Keywords: atropisomer; asymmetry; hydrogen bond; N-nitroso aldol reaction atropisomer; asymmetry; hydrogen bond; N-nitroso aldol reaction
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

Yeung, C.-T.; Chan, W.T.K.; Lo, W.-S.; Law, G.-L.; Wong, W.-T. Synthesis of a Conformationally Stable Atropisomeric Pair of Biphenyl Scaffold Containing Additional Stereogenic Centers. Molecules 2019, 24, 643.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top