Literature DB >> 26133693

Morita-Baylis-Hillman adduct derivatives (MBHADs): versatile reactivity in Lewis base-promoted annulation.

Peizhong Xie1, You Huang.   

Abstract

Lewis base-promoted annulation reactions with MBHADs have emerged as a key platform for the construction of functionalized carbo- and heterocycles. MBHADs, which are economical and readily available, exert diverse and amazing reactivity when reacted with a wide range of electrophiles. A variety of carbo- and heterocycles, most of which are predominant in natural products and pharmaceuticals, could be constructed with high efficiency. This tutorial review will describe these annulation reactions, with a special emphasis on recent work regarding diverse reactivities of MBHADs.

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Year:  2015        PMID: 26133693     DOI: 10.1039/c5ob00865d

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  10 in total

Review 1.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

2.  Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations.

Authors:  Yumei Xiao; Hongchao Guo; Ohyun Kwon
Journal:  Aldrichimica Acta       Date:  2016       Impact factor: 3.667

3.  Phosphine-catalyzed [5+1] annulation of δ-sulfonamido-substituted enones with N-sulfonylimines: a facile synthesis of tetrahydropyridines.

Authors:  Leijie Zhou; Chunhao Yuan; Yuan Zeng; Honglei Liu; Chang Wang; Xing Gao; Qijun Wang; Cheng Zhang; Hongchao Guo
Journal:  Chem Sci       Date:  2018-01-05       Impact factor: 9.825

Review 4.  Synthesis of chiral 3-substituted 3-amino-2-oxindoles through enantioselective catalytic nucleophilic additions to isatin imines.

Authors:  Hélène Pellissier
Journal:  Beilstein J Org Chem       Date:  2018-06-06       Impact factor: 2.883

5.  Catalytic Enantiodivergent Michael Addition by Subtle Adjustment of Achiral Amino Moiety of Dipeptide Phosphines.

Authors:  Huamin Wang; Xiuzheng Li; Youshao Tu; Junliang Zhang
Journal:  iScience       Date:  2020-05-06

6.  Phosphine-Catalyzed Dearomative [3 + 2] Cycloaddition of Benzoxazoles with a Cyclopropenone.

Authors:  Xingben Wang; Congjun Yu; Iuliana L Atodiresei; Frederic W Patureau
Journal:  Org Lett       Date:  2022-01-27       Impact factor: 6.005

7.  Asymmetric synthesis of multifunctional aryl allyl ethers by nucleophilic catalysis.

Authors:  Shuai Zhao; Lei Jin; Zhi-Li Chen; Xue Rui; Jia-Yi He; Ran Xia; Ke Chen; Xiang-Xiang Chen; Zi-Jian Yin; Xin Chen
Journal:  RSC Adv       Date:  2019-04-12       Impact factor: 4.036

8.  Phosphine-mediated enantioselective [1 + 4]-annulation of Morita-Baylis-Hillman carbonates with 2-enoylpyridines.

Authors:  Tao Wang; Pengfei Zhang; Wenjun Li; Pengfei Li
Journal:  RSC Adv       Date:  2018-12-12       Impact factor: 3.361

9.  Tri(n-butyl)phosphine-promoted domino reaction for the efficient construction of spiro[cyclohexane-1,3'-indolines] and spiro[indoline-3,2'-furan-3',3''-indolines].

Authors:  Hui Zheng; Ying Han; Jing Sun; Chao-Guo Yan
Journal:  Beilstein J Org Chem       Date:  2022-06-14       Impact factor: 2.544

10.  Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid.

Authors:  Weijun Yao; Zhaoyuan Yu; Shan Wen; Huanzhen Ni; Nisar Ullah; Yu Lan; Yixin Lu
Journal:  Chem Sci       Date:  2017-05-17       Impact factor: 9.825

  10 in total

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