Synthesis 2020; 52(07): 1131-1139
DOI: 10.1055/s-0039-1691643
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Chiral Tertiary Amine–Thioureas Based on Spirobi­indane and Application in Catalytic Asymmetric Michael Addition Reaction

Zhao Han
,
Xufeng Lin
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China   Email: lxfok@zju.edu.cn
› Author Affiliations
This work was funded by the National Natural Science Foundation of China (21572200).
Further Information

Publication History

Received: 19 November 2019

Accepted after revision: 18 December 2019

Publication Date:
04 February 2020 (online)


Abstract

A series of novel chiral bifunctional tertiary amine–thioureas based on spirobiindane were designed and synthesized as organo­catalysts. One of these catalysts was shown to promote the asymmetric Michael addition reaction of 1,3-diphenylpropane-1,3-dione to nitro­olefins, affording the desired products in good yields (up to 95%) and enantioselectivities (up to 98% ee).

Supporting Information

 
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