A novel method for the construction of (z,e)- or (z,z)-conjugated alkadienyl carboxylates.
[reaction: see text] The stereocontrolled dehydrobromination of 1,2-dibromoethyl carboxylates giving (Z)-2-bromovinyl carboxylates could readily be approached by using DBU and a catalytic amount of hydroquinone as a base at -78 degrees C. The first investigation on the Suzuki-type cross-coupling of (Z)-2-bromovinyl carboxylates as electrophiles with stereodefined alkenylboronic acids provides a novel method for the construction of (Z,E)- or (Z,Z)-conjugated alkadienyl carboxylate moieties, which are often present in a range of natural products.
He
Rong
R
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Academy of Sciences, 354 Fenglin Lu, P.R. China.
Deng
Min-Zhi
MZ