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Aza‐Diels–Alder reaction between cyclopentadiene and protonated N ‐phenylethyliminoacetates of 8‐phenylmenthol and 8‐phenyl neo menthol: a density functional theory study
Author(s) -
Miranda Margarida S.,
RodríguezBorges José E.,
Esteves da Silva Joaquim C. G.,
GarcíaMera Xerardo
Publication year - 2012
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1949
Subject(s) - cyclopentadiene , chemistry , density functional theory , cycloaddition , diels–alder reaction , protonation , isoprene , computational chemistry , selectivity , basis set , medicinal chemistry , organic chemistry , copolymer , catalysis , polymer , ion
The cycloaddition between glyoxylate imines possessing two chiral auxiliaries, N ‐( R )‐ or N ‐( S )‐1‐phenylethyl and 8‐phenylmenthyl or 8‐phenyl neo menthyl, and cyclopentadiene is described. Computational calculations using density functional theory with the Becke, three‐parameter, Lee–Yang–Parr functional and the 6‐31G(d) basis set were performed to better understand the highly diastereoselective mechanism and the exo ‐selectivity observed experimentally for these ionic aza‐Diels–Alder reactions. Copyright © 2011 John Wiley & Sons, Ltd.