Copper-Catalyzed γ-Selective and Stereospecific Substitution Reaction of Allylic Carbonates with Diboron: Efficient Route to Chiral Allylboron Compounds

Hajime Ito,* Chika Kawakami and Masaya Sawamura*

*Division of Chemistry, Graduate School of Science, Hokkaido University, and PRESTO, JST, Sapporo 060-0810, Japan, Email: hajitosci.hokudai.ac.jp, sawamurasci.hokudai.ac.jp

H. Ito, C. Kawakami, M. Sawamura, J. Am. Chem. Soc., 2005, 127, 16034-16035.

DOI: 10.1021/ja056099x (free Supporting Information)

---

Abstract

A copper-catalyzed γ-selective and stereospecific substitution reaction of allylic carbonates with bis(pinacolato)diboron afforded allylboron compounds. Functionalized allylboronates that have an acetal, ester, or isolated alkene were prepared. The reaction of optically active allylic carbonates underwent complete chirality transfer.

see article for more examples

---

---

Key Words

Boronates, Allylboronates, Copper Catalysis

---

ID: J48-Y2005-2680