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Diastereoselective intermolecular radical addition to nitrones.
Masafumi Ueda1, Hideto Miyabe, Masako Teramachi
1Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.
The Journal of Organic Chemistry
|August 13, 2005
Summary
Chiral nitrones undergo intermolecular radical addition with high stereocontrol. This study explores diastereoselective alkyl radical additions to various nitrones, yielding valuable synthetic intermediates.
Area of Science:
- Organic Chemistry
- Stereochemistry
- Radical Reactions
Background:
- Chiral nitrones are versatile synthons in organic synthesis.
- Controlling stereochemistry in radical additions is crucial for complex molecule synthesis.
Purpose of the Study:
- To investigate the intermolecular radical addition to chiral nitrones.
- To achieve high diastereoselectivity in these reactions.
- To evaluate the utility of different chiral nitrones and radical species.
Main Methods:
- Radical addition reactions to chiral nitrones (2, 4, 5, and 16).
- Utilized Oppolzer's camphorsultam derivative and cyclic nitrones.
- Employed various alkyl radicals and Lewis acids (Mg(ClO(4))(2)).
Main Results:
- Excellent diastereoselectivity observed in isopropyl radical addition to nitrone 2.
- High stereocontrol achieved with cyclic nitrone 4 using ethyl and other alkyl radicals.
- Selective syn isomer formation with BIGN 16 in the presence of Mg(ClO(4))(2).
- Anti isomer formation with BIGN 16 in the absence of Lewis acid.
Conclusions:
- Intermolecular radical addition to chiral nitrones is a powerful method for stereoselective synthesis.
- The choice of nitrone and reaction conditions significantly influences stereochemical outcomes.
- This methodology provides access to valuable chiral building blocks.