DFT Studies on the Stereoselectivity of α-Silyloxy Diazoalkane CycloadditionsReportar como inadecuado




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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

Abstract 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





Autor: Matthew J. O’Connor 1, Huaqing Liu 2, Daesung Lee 1,* , Tao Zhou 3 and Yuanzhi Xia 3,*

Fuente: http://mdpi.com/



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