Abstract
2,2-Dichloro- or 2,2-dibromovinylcyclopropane was condensed with electron-deficient alkenes in a phenylthio radical catalyzed process to afford 4-substituted and 4,5-disubstituted-l,l-dihalo-3-vinylcyclopentane derivatives in good yield and with good-to-excellent diastereoselectivity for the 3,4-cis isomer. Neither electron-rich nor β-substituted alkenes led to good yields of cyclopentane products. The diastereoselectivity and reactivity profiles of these transformations are satisfactorily rationalized by application of existing transition-state models of radical reactions.
Original language | English (US) |
---|---|
Pages (from-to) | 11364-11369 |
Number of pages | 6 |
Journal | Journal of the American Chemical Society |
Volume | 115 |
Issue number | 24 |
DOIs | |
State | Published - Dec 1 1993 |
All Science Journal Classification (ASJC) codes
- Catalysis
- General Chemistry
- Biochemistry
- Colloid and Surface Chemistry