Journal of the American Chemical Society 2008-03-05

Nickel-catalyzed asymmetric negishi cross-couplings of secondary allylic chlorides with alkylzincs.

Sunghee Son, Gregory C Fu

Index: J. Am. Chem. Soc. 130 , 2756, (2008)

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Abstract

Complementing previous advances in allylation chemistry, an effective nickel/Pybox catalyst for regioselective asymmetric Negishi cross-couplings of racemic secondary allylic chlorides with readily available organozinc halides has been developed. The method has been applied in two key steps of a formal total synthesis of fluvirucinine A1.

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(S)-BnCH2-PyBox, (S,S)-2,6-Bis(4-benzylmethyl-2-oxazolin-2-yl)pyridine Structure (S)-BnCH2-PyBox, (S,S)-2,6-Bis(4-benzylmethyl-2-oxazolin-2-yl)pyridine
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