Synfacts 2011(9): 1020-1020  
DOI: 10.1055/s-0030-1260921
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

[3+2] Annulation of MBH Adducts Promoted by Bifunctional Phosphines

Contributor(s): Benjamin List, Ji-Woong Lee
F. Zhong, X. Han, Y. Wang, Y. Lu*
National University of Singapore, Singapore and Henan University, Kaifeng, P. R. of China
Further Information

Publication History

Publication Date:
19 August 2011 (online)


Lu and co-workers report a highly enantioselective [3+2] annulation of MBH adducts 2 and isatin-derived activated alkenes 1. The reactions were promoted by bifunctional phosphine 3, which is easily accessible from threonine. Instead of commonly employed allenes and alkynes for [3+2] cycloadditions, the authors applied MBH adducts 2 as a C3 synthon. The obtained spiro­oxindoles 4 posses two contiguous quaternary centers with various functional groups. Also, a one-pot procedure with N-PMB-isatin and malononitrile under the reaction condition affords the desired product 4 with the same reactivity and enantioselectivity.