Literature DB >> 24000339

Organocatalyzed asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam.

Jinlong Zhang1, Xihong Liu, Xiaojuan Ma, Rui Wang.   

Abstract

Highly efficient asymmetric vinylogous 1,6-Michael addition of α,β-unsaturated γ-butyrolactam to 3-methyl-4-nitro-5-alkenyl-isoxazoles and Michael addition to trichloromethyl ketones by using a chiral quinine-derived squaramide organocatalyst were described, giving products with high diastereo- and enantioselectivities (up to >25 : 1 dr and 96% ee).

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Year:  2013        PMID： 24000339     DOI： 10.1039/c3cc44059a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  8 in total

1.  Tandem grinding reactions involving aldol condensation and Michael addition in sequence for synthesis of 3,4,5-trisubstituted isoxazoles.

Authors:  Xiao-Mu Hu; Hai Dong; Yue-Dan Li; Ping Huang; Zhuang Tian; Ping-An Wang
Journal:  RSC Adv       Date:  2019-09-04       Impact factor: 4.036

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.  Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters.

Authors:  Pankaj Chauhan; Suruchi Mahajan; Gerhard Raabe; Dieter Enders
Journal:  Chem Commun (Camb)       Date:  2015-02-11       Impact factor: 6.222

4.  [3+2] Cycloaddition of Tosylmethyl Isocyanide with Styrylisoxazoles: Facile Access to Polysubstituted 3-(Isoxazol-5-yl)pyrroles.

Authors:  Xueming Zhang; Xianxiu Xu; Dawei Zhang
Journal:  Molecules       Date:  2017-07-07       Impact factor: 4.411

5.  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

6.  Organocatalytic and enantioselective Michael reaction between α-nitroesters and nitroalkenes. Syn/anti-selectivity control using catalysts with the same absolute backbone chirality.

Authors:  Jose I Martínez; Uxue Uria; Maria Muñiz; Efraím Reyes; Luisa Carrillo; Jose L Vicario
Journal:  Beilstein J Org Chem       Date:  2015-12-14       Impact factor: 2.883

7.  Allylic-Allylic Alkylation with 3,5-Dimethyl-4-nitroisoxazole: A Route to Dicarboxylic Acid Derivatives.

Authors:  Dorota Kowalczyk-Dworak; Marcin Kwit; Łukasz Albrecht
Journal:  J Org Chem       Date:  2020-02-20       Impact factor: 4.354

8.  Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters.

Authors:  Chang Shu; Honglei Liu; Alexandra M Z Slawin; Cameron Carpenter-Warren; Andrew D Smith
Journal:  Chem Sci       Date:  2019-10-23       Impact factor: 9.825
  8 in total

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