Efficient Preparation of β-Branched γ,δ-Unsaturated Esters through Copper-Catalyzed Allylic Alkylation of Ketene Silyl Acetal

Dong Li, Hirohisa Ohmiya*, Masaya Sawamura*

*Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan, Email: ohmiyasci.hokudai.ac.jp, sawamurasci.hokudai.ac.jp

D. Li, H. Ohmiya, M. Sawamura, Synthesis, 2012, 44, 1304-1307.

DOI: 10.1055/s-0031-1289712

---

Abstract

Copper-catalyzed allylic alkylation of ketene silyl acetals proceeds with excellent γ-E-selectivity. In reactions of enantioenriched secondary allylic phosphates, an efficient α-to-γ chirality transfer with anti-selectivity can be achieved. The reaction was readily scalable and highly reliable in terms of product yield and stereoselectivities.

see article for more examples

---

---

Key Words

γ,δ-unsaturated esters, copper, allylic alkylation, ketene silyl acetal, regioselectivity

---

ID: J66-Y2012-1120