220115-62-8Relevant academic research and scientific papers
Preparation and reactions of masked allylic organozinc reagents
Jones, Philip,Knochel, Paul
, p. 186 - 195 (1999)
Allylic zinc reagents have been prepared from sterically hindered homoallylic alcohols 10 and 13, using a novel fragmentation reaction of the corresponding zinc alkoxide, without any homocoupling products. These allylic zinc reagents react with a range of electrophiles in good to excellent yields. Substituted allylic zinc reagents have also been prepared in this manner. α-Substituted homoallylic alcohols 37, 46, and 51 give solely α- substituted products after the fragmentation-allylation sequence; these products are obtained not only regioselectively but also with extremely high anti diastereoselectivity. Likewise, γ-substituted homoallylic alcohols 57 and 58, undergo the fragmentation-allylation reaction to give γ-substituted products. The reaction has also been demonstrated to be catalytic in zinc salts.
Highly diastereoselective reactions using masked allylic zinc reagents
Jones, Philip,Knochel, Paul
, p. 2407 - 2408 (2007/10/03)
Substituted allylic organozinc reagents have been prepared using a novel fragmentation reaction; the resulting allylic zinc species are configurationally stable and give excellent regio- and diastereo-selectivities.
