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- Title
Catalytic asymmetric carbon-carbon bond formation using alkenes as alkylmetal equivalents.
- Authors
Maksymowicz, Rebecca M.; Roth, Philippe M. C.; Fletcher, Stephen P.
- Abstract
Catalytic asymmetric conjugate addition reactions with organometallic reagents are powerful reactions in synthetic chemistry. Procedures that use non-stabilized carbanions have been developed extensively, but these suffer from a number of limitations that prevent their use in many situations. Here, we report that alkylmetal species generated in situ from alkenes can be used in highly enantioselective 1,4-addition initiated by a copper catalyst. Using alkenes as starting materials is desirable because they are readily available and have favourable properties when compared to pre-made organometallics. High levels of enantioselectivity are observed at room temperature in a range of solvents, and the reaction tolerates functional groups that are not compatible with comparable methods-a necessary prerequisite for efficient and protecting-group-free strategies for synthesis.
- Subjects
CARBON-carbon bonds; ALKENES; CATALYSIS; ORGANOMETALLIC compounds; CARBANIONS
- Publication
Nature Chemistry, 2012, Vol 4, Issue 8, p649
- ISSN
1755-4330
- Publication type
Article
- DOI
10.1038/nchem.1394