Mild and Efficient Diels-Alder Reaction Using Cationic Dienophiles Generated in situ
β Scribed by Yukihiko Hashimoto; Tadamichi Nagashima; Katsuhiro Kobayashi; Masaki Hasegawa; Kazuhiko Saigo
- Book ID
- 108371531
- Publisher
- Elsevier Science
- Year
- 1993
- Tongue
- French
- Weight
- 771 KB
- Volume
- 49
- Category
- Article
- ISSN
- 0040-4020
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π SIMILAR VOLUMES
Dienes readily undergo Diels-Alder reaction with CH 2 C(NO 2 )SO 2 Ph (2a), CH 2 C(NO 2 )CO 2 Et (2b), and CH 2 C(NO 2 )COPh (2c), all observed in situ by 1 H NMR. The cycloadducts of 2a undergo S RN 1 reactions.
The rate of Diels-Alder reactions with vinyll9-BBN is uniquely insensitive to diene substituent effects, and high reactivity is observed with both electron-rich and electron-poor dienes. The regioselectivity of these reactions is controlled mainly by steric effects. We recently reported that vinyld