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Synlett 2018; 29(15): 2006-2010
DOI: 10.1055/s-0037-1610232
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© Georg Thieme Verlag Stuttgart · New York

Chiral VAPOL Imidodiphosphoric Acid-Catalyzed Asymmetric Vinylogous Mannich Reaction for the Synthesis of Butenolides

Tianyun Zhou
a   College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China   Email: zhgl_jl@jlu.edu.cn   Email: suoqin@jlu.edu.cn
b   Key Laboratory for Molecular Enzymology and Engineering of Ministry of Education, College of Life Sciences, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China
,
Jigang Gao
a   College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China   Email: zhgl_jl@jlu.edu.cn   Email: suoqin@jlu.edu.cn
,
Guofeng Liu
a   College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China   Email: zhgl_jl@jlu.edu.cn   Email: suoqin@jlu.edu.cn
,
Xukai Guan
a   College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China   Email: zhgl_jl@jlu.edu.cn   Email: suoqin@jlu.edu.cn
,
Dong An
a   College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China   Email: zhgl_jl@jlu.edu.cn   Email: suoqin@jlu.edu.cn
,
Suoqin Zhang*
a   College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China   Email: zhgl_jl@jlu.edu.cn   Email: suoqin@jlu.edu.cn
b   Key Laboratory for Molecular Enzymology and Engineering of Ministry of Education, College of Life Sciences, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China
,
Guangliang Zhang*
a   College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China   Email: zhgl_jl@jlu.edu.cn   Email: suoqin@jlu.edu.cn
› Author Affiliations
We are grateful for financial support from the National Natural ­Science Foundation of China (Nos. 21372098 and 20802025) and the Jilin Province Science & Technology Development Program (Nos. 20150203006GX and 20140307004GX).
Further Information

Publication History

Received: 01 March 2018

Accepted after revision: 13 July 2018

Publication Date:
23 August 2018 (online)

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Abstract

Chiral butenolides were synthesized by the enantioselective vinylogous Mannich reaction. Chiral (VAPOL)-type imidodiphosphoric acids are efficient catalysts for the asymmetric vinylogous Mannich (AVM) reaction of aldimines and trimethylsiloxyfuran in toluene. Under the optimized conditions, a series of butenolides were obtained with high yields (up to 98%) and enantioselectivities (up to 97% ee) as well as excellent diastereoselectivities (up to 99:1 dr).

Key words

butenolides - trimethylsiloxyfuran - organocatalysis - enantio­selectivity - asymmetric vinylogous Mannich reaction

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610232.
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