Details

Autor(en) / Beteiligte

• Marek, Ilan
• Schreiner, Peter R
• Normant, Jean F

Titel

Allyl Zincation of Vinyl Metals:  A Computational Study

Ist Teil von

• Organic letters, 1999-09, Vol.1 (6), p.929-931

Ort / Verlag

American Chemical Society

Erscheinungsjahr

1999

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• The allyl zincation of vinyllithium or Grignard reagents was studied computationally and compared to the allyl zincation of ethylene. The key step is a preorganization of the reagents via Zn−Br−Li (or Mg) coordination, which is also apparent in the transition structures. The experimentally observed diastereoselectivity when substituted (E)- or (Z)-vinyllithium reagents are added to crotylzinc bromide may also be explained in terms of preferentially stabilized transition structures with cisoid allyl moieties.