Literature DB >> 21332151

L-threonine-derived novel bifunctional phosphine-sulfonamide catalyst-promoted enantioselective aza-Morita-Baylis-Hillman reaction.

Fangrui Zhong1, Youqing Wang, Xiaoyu Han, Kuo-Wei Huang, Yixin Lu.   

Abstract

A series of novel bifunctional phosphine-sulfonamide organic catalysts were designed and readily prepared from natural amino acids, and they were utilized to promote enantioselective aza-Morita-Baylis-Hillman (MBH) reactions. L-threonine-derived phosphine-sulfonamide 9b was found to be the most efficient catalyst, affording the desired aza-MBH adducts in high yields and with excellent enantioselectivities.

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Year:  2011        PMID: 21332151     DOI: 10.1021/ol103145g

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


  5 in total

1.  Asymmetric catalytic aza-Morita-Baylis-Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers.

Authors:  Fang-Le Hu; Yin Wei; Min Shi; Suresh Pindi; Guigen Li
Journal:  Org Biomol Chem       Date:  2013-02-13       Impact factor: 3.876

2.  Phosphine-catalyzed divergent domino processes between γ-substituted allenoates and carbonyl-activated alkenes.

Authors:  Mingyue Wu; Zhaobin Han; Huanzhen Ni; Nengzhong Wang; Kuiling Ding; Yixin Lu
Journal:  Chem Sci       Date:  2022-02-11       Impact factor: 9.825

3.  Enantioselective [3 + 2] annulation of α-substituted allenoates with β,γ-unsaturated N-sulfonylimines catalyzed by a bifunctional dipeptide phosphine.

Authors:  Huanzhen Ni; Weijun Yao; Yixin Lu
Journal:  Beilstein J Org Chem       Date:  2016-02-24       Impact factor: 2.883

4.  Chiral phosphine-catalyzed tunable cycloaddition reactions of allenoates with benzofuranone-derived olefins for a highly regio-, diastereo- and enantioselective synthesis of spiro-benzofuranones.

Authors:  Guo-Peng Wang; Yao-Liang Sun; Shou-Fei Zhu; Yin Wei; Qi-Lin Zhou; Min Shi
Journal:  Chem Sci       Date:  2015-09-15       Impact factor: 9.825

5.  Catalyst-controlled regioselectivity in phosphine catalysis: the synthesis of spirocyclic benzofuranones via regiodivergent [3 + 2] annulations of aurones and an allenoate.

Authors:  Huanzhen Ni; Zhaoyuan Yu; Weijun Yao; Yu Lan; Nisar Ullah; Yixin Lu
Journal:  Chem Sci       Date:  2017-06-12       Impact factor: 9.825

  5 in total

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