Synfacts 2009(10): 1165-1165  
DOI: 10.1055/s-0029-1218014
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Construction of Spirocyclic Oxindoles by Aminocatalysis Cascades

Contributor(s): Benjamin List, Ilija Èorić
G. Bencivenni, L.-Y. Wu, A. Mazzanti, B. Giannichi, F. Pesciaioli, M.-P. Song, G. Bartoli, P. Melchiorre*
Università di Bologna, Italy and Zhengzhou University, P. R. of China
Further Information

Publication History

Publication Date:
22 September 2009 (online)

Significance

Aminocatalysis cascade reactions were employed for one-step construction of complex spirocyclic oxindoles 4 and 9. Starting from oxindoles 2 and α,β-unsaturated ketones 3 using primary amine catalyst 1 spirocyclic oxindoles 4 were obtained in moderate yields with high enan­tioselectivity. A complementary three-component reaction starting from oxindoles 6, aldehydes 7 and α,β-unsaturated aldehydes 8 was catalyzed by secondary amine catalyst 5. Spirocyclic oxindoles 9 were obtained in moderate yields with very high enantioselectivity.