Literature DB >> 22453359

Organocatalytic asymmetric transformations of modified Morita-Baylis-Hillman adducts.

Tian-Yu Liu1, Min Xie, Ying-Chun Chen.   

Abstract

Chiral Lewis basic tertiary amines or phosphines can enable properly modified Morita-Baylis-Hillman (MBH) adducts to undergo asymmetric allylic substitutions with a wide range of nucleophiles. In addition, assisted by a Brønsted base, chiral Lewis bases can also catalytically convert modified MBH adducts into allylic ylides, which can be engaged in a variety of asymmetric annulation reactions. This tutorial review will focus on such chiral Lewis base-catalysed asymmetric transformations of MBH adducts, especially those developed over the past five years, allowing for the rapid construction of densely functionalised chiral molecules with high levels of regio- and stereoselectivities.

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Year:  2012        PMID: 22453359     DOI: 10.1039/c2cs35017c

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  12 in total

Review 1.  The ever-expanding role of asymmetric covalent organocatalysis in scalable, natural product synthesis.

Authors:  Mikail E Abbasov; Daniel Romo
Journal:  Nat Prod Rep       Date:  2014-10       Impact factor: 13.423

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

Review 3.  Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.

Authors:  Bin Mao; Martín Fañanás-Mastral; Ben L Feringa
Journal:  Chem Rev       Date:  2017-06-22       Impact factor: 60.622

4.  Regio- and Stereoselective Electrochemical Alkylation of Morita-Baylis-Hillman Adducts.

Authors:  Giulio Bertuzzi; Giada Ombrosi; Marco Bandini
Journal:  Org Lett       Date:  2022-06-14       Impact factor: 6.072

5.  Organocatalytic asymmetric allylic amination of Morita-Baylis-Hillman carbonates of isatins.

Authors:  Hang Zhang; Shan-Jun Zhang; Qing-Qing Zhou; Lin Dong; Ying-Chun Chen
Journal:  Beilstein J Org Chem       Date:  2012-08-06       Impact factor: 2.883

6.  Morita-Baylis-Hillman reaction of acrylamide with isatin derivatives.

Authors:  Radhey Mohan Singh; Kishor Chandra Bharadwaj; Dharmendra Kumar Tiwari
Journal:  Beilstein J Org Chem       Date:  2014-12-12       Impact factor: 2.883

7.  Photoswitchable interlocked thiodiglycolamide as a cocatalyst of a chalcogeno-Baylis-Hillman reaction.

Authors:  Alberto Martinez-Cuezva; Adrian Saura-Sanmartin; Tomas Nicolas-Garcia; Cristian Navarro; Raul-Angel Orenes; Mateo Alajarin; Jose Berna
Journal:  Chem Sci       Date:  2017-03-07       Impact factor: 9.825

8.  Asymmetric phase-transfer catalysed β-addition of isoxazolidin-5-ones to MBH carbonates.

Authors:  Vito Capaccio; Katharina Zielke; Andreas Eitzinger; Antonio Massa; Laura Palombi; Kirill Faust; Mario Waser
Journal:  Org Chem Front       Date:  2018-10-12       Impact factor: 5.281

9.  Asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates with α-fluoro-β-keto esters.

Authors:  Lin Yan; Zhiqiang Han; Bo Zhu; Caiyun Yang; Choon-Hong Tan; Zhiyong Jiang
Journal:  Beilstein J Org Chem       Date:  2013-09-11       Impact factor: 2.883

Review 10.  Chiral phosphines in nucleophilic organocatalysis.

Authors:  Yumei Xiao; Zhanhu Sun; Hongchao Guo; Ohyun Kwon
Journal:  Beilstein J Org Chem       Date:  2014-09-04       Impact factor: 2.883

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