Literature DB >> 11506631

Tandem zirconocene homologation-aldimine allylation.

P Wipf1, C Kendall.   

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.

Entities:  

Year:  2001        PMID： 11506631     DOI： 10.1021/ol0163880

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  Preparation of stereodefined homoallylic amines from the reductive cross-coupling of allylic alcohols with imines.

Authors:  Ming Z Chen; Martin McLaughlin; Masayuki Takahashi; Michael A Tarselli; Dexi Yang; Shuhei Umemura; Glenn C Micalizio
Journal:  J Org Chem       Date:  2010-11-11       Impact factor: 4.354

2.  Complex allylation by the direct cross-coupling of imines with unactivated allylic alcohols.

Authors:  Masayuki Takahashi; Martin McLaughlin; Glenn C Micalizio
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  Homoallylic amines by reductive inter- and intramolecular coupling of allenes and nitriles.

Authors:  Peter Wipf; Marija D Manojlovic
Journal:  Beilstein J Org Chem       Date:  2011-06-17       Impact factor: 2.883
  3 in total

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