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. 2001 Aug 23;3(17):2773-6.
doi: 10.1021/ol0163880.

Tandem zirconocene homologation-aldimine allylation

P Wipf  1 , C Kendall
Affiliations

Tandem zirconocene homologation-aldimine allylation

P Wipf et al. Org Lett. .

Abstract

[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.

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