Vinylboranes are omniphilic dienophiles. Some unusual and useful properties of vinylboranes in diels-alder reactions
✍ Scribed by Daniel A. Singleton; Jose P. Martinez; José V. Watson
- Book ID
- 104224916
- Publisher
- Elsevier Science
- Year
- 1992
- Tongue
- French
- Weight
- 285 KB
- Volume
- 33
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
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 vinyldialkylboranes are exceptionally reactive, regioselective, and endustereoselective Diels-Alder dienophiles. 1 This discovery was based on the old idea that a trivalent boron atom should behave in a fashion similar to traditional organic electron-withdrawing groups.2 The application of this