TY - JOUR
T1 - Recognition-induced control of a Diels-Alder cycloaddition
AU - Robertson, Andrew
AU - Philp, Douglas
AU - Spencer, Neil
N1 - Funding Information:
This research was supported by the University of Birmingham, the Engineering and Physical Sciences Research Council (Quota Award to A.R.), and the Biotechnology and Biological Sciences Research Council (Grants 6/B03840 and 6/B04100). We thank Prof G. yon Kiedrowski for supplying us with a copy of his SimFit program.
PY - 1999/9/10
Y1 - 1999/9/10
N2 - The rational design of systems which are capable of accelerating and/or controlling the stereochemical outcome of the Diels-Alder cycloaddition reaction between a furan and a maleimide is presented. The origins of the acceleration and control of the cycloaddition reactions are traced by kinetic studies - allied to molecular mechanics calculations - to the formation of complexes in which the dienes and the dieneophiles are placed in the appropriate arrangements for reaction, and, more importantly, to the formation of intramolecular hydrogen bonds in the cycloadducts.
AB - The rational design of systems which are capable of accelerating and/or controlling the stereochemical outcome of the Diels-Alder cycloaddition reaction between a furan and a maleimide is presented. The origins of the acceleration and control of the cycloaddition reactions are traced by kinetic studies - allied to molecular mechanics calculations - to the formation of complexes in which the dienes and the dieneophiles are placed in the appropriate arrangements for reaction, and, more importantly, to the formation of intramolecular hydrogen bonds in the cycloadducts.
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U2 - 10.1016/S0040-4020(99)00633-X
DO - 10.1016/S0040-4020(99)00633-X
M3 - Article
AN - SCOPUS:0033543474
SN - 0040-4020
VL - 55
SP - 11365
EP - 11384
JO - Tetrahedron
JF - Tetrahedron
IS - 37
ER -