Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
4 years ago

Catalytic Asymmetric Mannich Reaction with N-Carbamoyl Imine Surrogates of Formaldehyde and Glyoxylate

Catalytic Asymmetric Mannich Reaction with N-Carbamoyl Imine Surrogates of Formaldehyde and Glyoxylate
Long Zhang, Yang'en You, Sanzhong Luo, Xueling Mi, Linfeng Cui
N,O-acetals (NOAcs) were developed as bench stable surrogates for N-carbamoyl, (Boc, Cbz and Fmoc) formaldehyde and glyoxylate imines in asymmetric Mannich reactions. The NOAcs can be directly utilized in the chiral primary amine catalyzed Mannich reactions of both acyclic and cyclic β-ketocarbonyls with high yields and excellent stereoselectivity. The current reaction offers a straightforward approach in the asymmetric synthesis of α- or β-amino carbonyls bearing chiral quaternary centers in a practical and highly stereocontrolled manner. On the bench: N,O-acetals (NOAcs) were developed as bench-stable surrogates for N-carbamoyl (Boc, Cbz, Fmoc) formaldehyde and glyoxylate imines in asymmetric Mannich reactions. This reaction offers a straightforward approach for the asymmetric synthesis of α- or β-amino carbonyls bearing chiral quaternary centers in a practical and highly stereocontrolled manner. EWG=electron-withdrawing group, PG=protecting group.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201707005

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