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A new approach to the asymmetric Mannich reaction catalyzed by chiral N,N'-dioxide-metal complexes.

ABSTRACT: A highly efficient asymmetric Mannich-type reaction between ?-tetralone-derived ?-keto esters/amides and 1,3,5-triaryl-1,3,5-triazinanes was realized in the presence of chiral N,N'-dioxide-Ni(ii) or Mg(ii) complex. A variety of optically active ?-amino compounds with all-carbon quaternary stereocenters were obtained in good yields with excellent enantioselectivities. A possible transition state was proposed based on these experiments and previous reports.

SUBMITTER: Lian X

PROVIDER: S-EPMC5369522 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

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A new approach to the asymmetric Mannich reaction catalyzed by chiral N,N'-dioxide-metal complexes.

Lian Xiangjin X Lin Lili L Fu Kai K Ma Baiwei B Liu Xiaohua X Feng Xiaoming X

Chemical science 20161003 2

A highly efficient asymmetric Mannich-type reaction between α-tetralone-derived β-keto esters/amides and 1,3,5-triaryl-1,3,5-triazinanes was realized in the presence of chiral N,N'-dioxide-Ni(ii) or Mg(ii) complex. A variety of optically active β-amino compounds with all-carbon quaternary stereocenters were obtained in good yields with excellent enantioselectivities. A possible transition state was proposed based on these experiments and previous reports. ...[more]

PMID: 28451265

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