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DFT Studies on the Stereoselectivity of α-Silyloxy Diazoalkane Cycloadditions.

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journal contribution
posted on 10.05.2016 by MJ O'Connor, H Liu, D Lee, T Zhou, Y Xia
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).

Funding

Financial support for this research from NSF (CHE 0955972, D.L.) and NSFC (21372178 and 21572163, Y.X.).

History

Publisher Statement

This is a copy of an article published in Molecules © 2015 MDPI Publications.

Publisher

MDPI

issn

1420-3049

Issue date

02/12/2015

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