Catalytic asymmetric carbon-carbon bond formation using alkenes as alkylmetal equivalents

Autor: Stephen P. Fletcher, Philippe M. C. Roth, Rebecca M. Maksymowicz
Jazyk: angličtina
Rok vydání: 2016
Předmět:
DOI: 10.1038/nchem.1394
Popis: 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.
Databáze: OpenAIRE