Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative

• Toshiki Tabuchi,
• Daisuke Urabe and
• Masayuki Inoue

Beilstein J. Org. Chem. 2013, 9, 655–663, doi:10.3762/bjoc.9.74

• -dimethylbenzene-1,4-diol (3) and maleic anhydride lead to the construction of bicyclo[2.2.2]octene 4, which was then transformed into racemic 2 through electrolysis [11]. Alternatively, the Diels–Alder reaction between 3,6-dimethyl-o-quinone monoacetal 5 and 1,1-diethoxyethylene provided bicyclo[2.2.2]octene 6

Catalytic synthesis of (E)-α,β-unsaturated esters from aldehydes and 1,1-diethoxyethylene

• Rubén Manzano,
• Lidia Ozores,
• Andreas Job,
• Lars Rodefeld and
• Benjamin List

Beilstein J. Org. Chem. 2009, 5, No. 3, doi:10.3762/bjoc.5.3

• high yielding synthesis of α,β-unsaturated esters from aldehydes and 1,1-diethoxyethylene was developed. Keywords: 1,1-diethoxyethylene; α,β-unsaturated esters; Introduction A number of reactions transforming aldehydes into α,β-unsaturated esters have been developed and especially Wittig reaction

• this particular boronic acid, which possesses both Lewis acidity and Brønsted acidity, was the most active catalyst and gave the highest yields of the corresponding α,β-unsaturated ester. The optimized procedure involved the slow addition of 1,1-diethoxyethylene to benzaldehyde in the presence of a