Next Article in Journal
Enrichment and Purification of Polyphenol Extract from Sphallerocarpus gracilis Stems and Leaves and in Vitro Evaluation of DNA Damage-Protective Activity and Inhibitory Effects of α-Amylase and α-Glucosidase
Next Article in Special Issue
1,3-Dipolar Cycloaddition in the Preparation of New Fused Heterocyclic Compounds via Thermal Initiation
Previous Article in Journal
Accurate Mass GC/LC-Quadrupole Time of Flight Mass Spectrometry Analysis of Fatty Acids and Triacylglycerols of Spicy Fruits from the Apiaceae Family
Open AccessCommunication

DFT Studies on the Stereoselectivity of α-Silyloxy Diazoalkane Cycloadditions

1
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago 60607, IL, USA
2
Abbvie Inc., 1 North Waukegan Road, North Chicago 60064, IL, USA
3
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Mark Rizzacasa
Molecules 2015, 20(12), 21433-21441; https://doi.org/10.3390/molecules201219783
Received: 14 October 2015 / Revised: 18 November 2015 / Accepted: 26 November 2015 / Published: 2 December 2015
(This article belongs to the Special Issue Pericyclic Reactions)
The intramolecular [3+2] cycloaddition (32CA) of alkene-tethered α-silyloxydiazoalkanes provides variable stereoselectivity in generating bicyclic pyrazolines where the silyloxy group is either syn or anti to the newly formed pyrazoline ring. To elucidate the origin of the stereoselectivity, density functional theory (DFT) calculations were carried out for the energy of each transition state structure (TSs) and product. Steric effects were identified as the major determining factors in the diastereoselectivity of the 32CA reaction with regards to substrate structure (cyclic or acyclic α-silyloxydiazoalkanes). View Full-Text
Keywords: density functional theory; diazoalkane; [3+2] cycloaddition; gauche effect; stereoselectivity density functional theory; diazoalkane; [3+2] cycloaddition; gauche effect; stereoselectivity
Show Figures

Graphical abstract

MDPI and ACS Style

O’Connor, M.J.; Liu, H.; Lee, D.; Zhou, T.; Xia, Y. DFT Studies on the Stereoselectivity of α-Silyloxy Diazoalkane Cycloadditions. Molecules 2015, 20, 21433-21441.

Show more citation formats Show less citations formats

Article Access Map by Country/Region

1
Search more from Scilit
 
Search
Back to TopTop