Dec, 2003
Dipole interaction-controlled stereoselectivity in aldol reaction of alpha-CF3 enolate with fluoral
ORGANIC LETTERS
- ,
- ,
- Volume
- 5
- Number
- 25
- First page
- 4807
- Last page
- 4809
- Language
- English
- Publishing type
- Research paper (scientific journal)
- DOI
- 10.1021/ol0358307
- Publisher
- AMER CHEMICAL SOC
[GRAPHICS]
The stereoselectivity of a reaction is generally determined by minimizing steric repulsion. However, the aldol reaction of alpha-CF3-ketone (Z)-enolate with fluoral anomalously gave an anti-aldol through a sterically demanding transition state, because of the strong dipole interaction of the two CF3 groups. We have thus disclosed a paradigm shift from steric to electronic control of reaction stereoselectivity.
The stereoselectivity of a reaction is generally determined by minimizing steric repulsion. However, the aldol reaction of alpha-CF3-ketone (Z)-enolate with fluoral anomalously gave an anti-aldol through a sterically demanding transition state, because of the strong dipole interaction of the two CF3 groups. We have thus disclosed a paradigm shift from steric to electronic control of reaction stereoselectivity.
- Link information
- ID information
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- DOI : 10.1021/ol0358307
- ISSN : 1523-7060
- Web of Science ID : WOS:000187038300014