Organocatalytic Diversity-Oriented Asymmetric Synthesis of Tricyclic Chroman Derivatives

The tandem oxo-Michael-IED/HDA and oxo-Michael-IED/HDA-Michael-Aldol condensation transformations between (E)-2-hydroxyaryl-2-oxobut-3-enoate derivatives with enals have been developed in the presence of (S)-diphenylprolinol trimethylsilyl ether as an organocatalyst. Two types of tricyclic chroman d...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-11, Vol.79 (22), p.10772-10785
Main Authors: Geng, Zhi-Cong, Zhang, Shao-Yun, Li, Nai-Kai, Li, Ning, Chen, Jian, Li, Hai-Yan, Wang, Xing-Wang
Format: Article
Language:English
Subjects:
Butyrates - chemistry
Catalysis
Chromans - chemical synthesis
Chromans - chemistry
Ethers - chemistry
Molecular Structure
Pyrrolidines - chemistry
Stereoisomerism
Trimethylsilyl Compounds - chemistry
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Summary:The tandem oxo-Michael-IED/HDA and oxo-Michael-IED/HDA-Michael-Aldol condensation transformations between (E)-2-hydroxyaryl-2-oxobut-3-enoate derivatives with enals have been developed in the presence of (S)-diphenylprolinol trimethylsilyl ether as an organocatalyst. Two types of tricyclic chroman derivatives were, respectively, obtained, by adjusting the reactant ratio and reaction temperature, in good yields (up to 96%) with excellent enantioselectivities (up to >99%) and good diastereoselectivities (up to >30/1). It should be noted that the divergent chiral chroman derivatives were obtained by successive reaction of (E)-2-hydroxy­aryl-2-oxobut-3-enoate derivatives with two different enal substrates in highly catalytic results.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo501560m