Diels-Alder cycloadditions of rigid dienophiles: A probe for allylic axial substituent control of the pi-facial selectivity in the Diels-Alder reaction
✍ Scribed by Dale L. Boger; Mona Patel
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 200 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A study of t he p i-fa c ial sel e ctivit y o f the Diels -Alder reaction of N -ben~oyl 5methox ycarbonyl-2-a~a-oxabi cyclo[2 .2.2]oct-4-ene, a rigid electron de f i cie nt dienoph i l e bearing t wo allylic axial heteroat om subst ituents, with I -me thoxy-3-trimet h ylsil yl oxybut adi ene , a r epresentative ele ctron ri ch diene, i s d etail ed.
📜 SIMILAR VOLUMES
p-Facial selectivity in Diels-Alder reactions of cyclopentadienes having C( O)YR substituents at the 5-positions was predicted on the basis of the orbital mixing rule and was substantiated experimentally. The selectivity was disclosed to be highly dependent on the relative orbital energy between p H
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