Literature DB >> 22471756

Diastereo- and enantioselective [3 + 2] cycloaddition reaction of Morita-Baylis-Hillman carbonates of isatins with N-phenylmaleimide catalyzed by Me-DuPhos.

Yan Wang1, Li Liu, Tao Zhang, Neng-Jun Zhong, Dong Wang, Yong-Jun Chen.   

Abstract

A Me-DuPhos-catalyzed efficient asymmetric [3 + 2] cycloaddition reaction between Morita-Baylis-Hillman carbonates of isatins and N-phenylmaleimide has been developed. This reaction constructs three chiral centers in one step to afford spirocyclopentaneoxindoles in good yields (up to 84%) with excellent diastereo- and enantioselectivies (up to 99% ee).
© 2012 American Chemical Society

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Year:  2012        PMID： 22471756     DOI： 10.1021/jo3002535

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  6 in total

1.  Copper(II)- and palladium(II)-catalyzed enantioselective Claisen rearrangement of allyloxy- and propargyloxy-indoles to quaternary oxindoles and spirocyclic lactones.

Authors:  Trung Cao; Elizabeth C Linton; Joshua Deitch; Simon Berritt; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2012-12-04       Impact factor: 4.354

Review 2.  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

Review 3.  Molecular diversity of spirooxindoles. Synthesis and biological activity.

Authors:  Tetyana L Pavlovska; Ruslan Gr Redkin; Victoria V Lipson; Dmytro V Atamanuk
Journal:  Mol Divers       Date:  2015-09-29       Impact factor: 2.943

4.  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

5.  Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael-Henry cascade reactions.

Authors:  Yonglei Du; Jian Li; Kerong Chen; Chenglin Wu; Yu Zhou; Hong Liu
Journal:  Beilstein J Org Chem       Date:  2017-07-07       Impact factor: 2.883

6.  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
  6 in total

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