Chiral VAPOL Imidodiphosphoric Acid-Catalyzed Asymmetric Vinylogous Mannich Reaction for the Synthesis of Butenolides-Reference-Cited by-同舟云学术

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

Published:2018-08-23 Issue:15 Volume:29 Page:2006-2010
ISSN:0936-5214
Container-title:Synlett
language:en
Short-container-title:Synlett

Author:

Zhang Suoqin¹²,Zhang Guangliang¹,Zhou Tianyun¹²,Gao Jigang¹,Liu Guofeng¹,Guan Xukai¹,An Dong¹

Affiliation:

1. College of Chemistry, Jilin University

2. Key Laboratory for Molecular Enzymology and Engineering of Ministry of Education, College of Life Sciences, Jilin University

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).

Funder

National Natural Science Foundation of China

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0037-1610232.pdf

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