Diastereoselection in the conjugate additions of organocopper reagents to N-enoyloxazolidinones
โ Scribed by David R Williams; William S Kissel; Jie Jack Li
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 257 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
A survey of conjugate additions of Yamamoto organocopper reagents to N-enoyl-4-substituted oxazolidinones is reported. Diastereofacial selectivity is reversed for 4-phenyl and 4-benzyloxazolidinones of the same relative configuration. Alkenylcopper reagents demonstrate superior results in asymmetric additions using the 4-phenyloxazolidinone auxiliary.
๐ SIMILAR VOLUMES
Mediated by a noncovalently bound chiral amidophosphine iigand I, reaction of organocoppers with cycloalkenones 2 aforded the corresponding J-substituted cyclo-aLk-anones 3 in 9568% ee.
N-Tosylated cx, S-unsaturated amides and lactams undergo facile conjugate addition with R'CuLi or RMgX/CuI (cat.). Stereoselective synthesis of trans-S,y-dialkyl-y-lactams