Aminocatalytic asymmetric exo-Diels-Alder reaction with methiodide salts of Mannich bases and 2,4-dienals to construct chiral spirocycles.

Shan-Jun Zhang, Jun Zhang, Qing-Qing Zhou, Lin Dong, Ying-Chun Chen

Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.

Organic letters 2013 Feb 15

filter terms:

An asymmetric exo-Diels-Alder reaction of α-methylene carbonyl compounds, generated in situ from stable methiodide salts of Mannich bases, with 2,4-dienals, has been developed through trienamine activation of a chiral secondary amine. A spectrum of spirocyclanes with high molecular complexity was efficiently constructed in moderate to excellent diastereo- and enantioselectivity.

Citation

Shan-Jun Zhang, Jun Zhang, Qing-Qing Zhou, Lin Dong, Ying-Chun Chen. Aminocatalytic asymmetric exo-Diels-Alder reaction with methiodide salts of Mannich bases and 2,4-dienals to construct chiral spirocycles. Organic letters. 2013 Feb 15;15(4):968-71