Literature DB >> 22087591

Bifunctional 3,3'-Ph2-BINOL-Mg catalyzed direct asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam.

Li Lin1, Jinlong Zhang, Xiaojuan Ma, Xu Fu, Rui Wang.   

Abstract

Bifunctional 3,3'-Ph(2)-BINOL-Mg catalyzed direct asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam has been developed. The catalytic activity of this protocol was slightly affected by different types of Michael acceptors, such as a variety of enones as well as α,β-unsaturated N-acylpyrroles. The Michael products were obtained with high diastereoselectivities (up to 20:1) and excellent enantioselectivities (up to 98%).

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Year:  2011        PMID: 22087591     DOI: 10.1021/ol202713f

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

1.  Mild and rapid hydroxylation of aryl/heteroaryl boronic acids and boronate esters with N-oxides.

Authors:  Chen Zhu; Rui Wang; J R Falck
Journal:  Org Lett       Date:  2012-06-26       Impact factor: 6.005

2.  Direct Catalytic Asymmetric Doubly Vinylogous Michael Addition of α,β-Unsaturated γ-Butyrolactams to Dienones.

Authors:  Xiaodong Gu; Tingting Guo; Yuanyuan Dai; Allegra Franchino; Jie Fei; Chuncheng Zou; Darren J Dixon; Jinxing Ye
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-15       Impact factor: 15.336

3.  Direct β-selectivity of α,β-unsaturated γ-butyrolactam for asymmetric conjugate additions in an organocatalytic manner.

Authors:  Yuan Zhong; Sihua Hong; Zhengjun Cai; Shixiong Ma; Xianxing Jiang
Journal:  RSC Adv       Date:  2018-08-14       Impact factor: 4.036

4.  Diastereoselective radical addition to γ-alkyl-α-methylene-γ-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative.

Authors:  Tomoko Yajima; Eriko Yoshida; Masako Hamano
Journal:  Beilstein J Org Chem       Date:  2013-07-17       Impact factor: 2.883

  4 in total

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