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Orbital control of π-facial selectivity in Diels–Alder reactions of cyclopentadienes having C(O)YR substituents at the 5-positions

✍ Scribed by Masaru Ishida; Masakazu Sakamoto; Humihiro Hattori; Minako Shimizu; Satoshi Inagaki

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 193 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)00421-x

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✦ Synopsis

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 HOMO of the diene and n Y of the substituent.

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