Tandem zirconocene homologation-aldimine allylation.
[reaction: see text]. Hydrozirconation of internal and terminal alkynes followed by in situ transmetalation to dimethylzinc and treatment with diiodomethane leads to chain extended allylic organometallics. Addition to N-phosphinoyl or N-sulfonyl aldimines provides homoallylic amines in 48-87% yield and 3:2 to >20:1 diastereomeric ratios favoring anti-products.
Wipf
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P
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA. pwipf+@pitt.edu
Kendall
C
C