Asymmetric addition of 3-substituted benzofuran-2-ones to isatin N-Boc ketimines catalyzed by chiral biscinchona alkaloid catalyst

A highly enantioselective Mannich reaction of 3-substituted benzofuran-2(3H)-ones and isatin N-Boc ketimines catalyzed by a chiral biscinchona alkaloid catalyst was developed, which proved to be an efficient way for the synthesis of chiral 3,3′-disubstituted benzofuran-2-one derivatives. The nucleop...

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Bibliographic Details
Published inTetrahedron Vol. 71; no. 24; pp. 4090 - 4097
Main Authors Zhu, Yi, Zhang, Enge, Luo, Chao, Li, Xin, Cheng, Jin-Pei
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.06.2015
Elsevier
Subjects
Benzofuranone
Chemistry
Chemistry, Organic
Mannich reaction
N-Boc ketimine
Organocatalysis
Oxindole
Physical Sciences
Science & Technology
Oxindole
Benzofuranone
Organocatalysis
N-Boc ketimine
Mannich reaction
ACID
ENANTIOSELECTIVE SYNTHESIS
IMINES
PICTET-SPENGLER REACTIONS
MICHAEL ADDITION
BENZOFURAN-2(3H)-ONES
BIFUNCTIONAL THIOUREA
CONSTRUCTION
CONJUGATE ADDITIONS
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Summary:A highly enantioselective Mannich reaction of 3-substituted benzofuran-2(3H)-ones and isatin N-Boc ketimines catalyzed by a chiral biscinchona alkaloid catalyst was developed, which proved to be an efficient way for the synthesis of chiral 3,3′-disubstituted benzofuran-2-one derivatives. The nucleophilic addition products were generally obtained in high yields (up to 99%) with very good diastereoselectivities (up to >95:5 dr) and enantioselectivities (up to 98% ee). [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.04.114