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Zirconocenes vs. Alanes: a Crucial Choice of the Allyl Source for Highly Diastereoselective Allylzincation of Nonracemic Chiral Imines
Author(s) -
Coffinet Michael,
Jaroschik Florian,
Vasse JeanLuc
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600214
Subject(s) - transmetalation , chemistry , stereoselectivity , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis
An efficient in‐situ generation of allylzinc compounds from allylzirconocenes applied to the allylmetallation of phenylglycinol‐derived imines is described. The key advantage of the method lies in the concomitant formation of a zirconocene during the Zr–Zn transmetallation step, which appears to be beneficial for the stereoselectivity of the reaction. In the specific case of coupling of imines with racemic chiral allylzinc compounds, this method provides highly diastereoselective access to valuable enantiomerically enriched amines with high synthetic potential.