Literature DB >> 27859806

Catalytic Strategies for Diastereodivergent Synthesis.

Lili Lin1, Xiaoming Feng1.   

Abstract

Chiral molecules with multiple stereocenters are widely distributed in nature and drugs. Asymmeric catalysis has allowed the formation of a chiral molecule's enantiomers with equal ease by applying the enantiomeric pair of a chiral catalyst. However, the diastereodivergent synthesis is a great challenge because the formation of one of the diastereomers is inherently preferred in most reactions. Under the efforts of chemists, elegant strategies have been developed to full control of absolute and relative stereochemical configurations. In this Minireview, we highlight the significant advances achieved in this field, and present the diastereo-control mechanism in the appropriate place on the expectation that new diastereodivergent strategies can be inspired and more types of enantioselective diastereodivergent reactions can be realized.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords:  asymmetric catalysis; diastereodivergency; enantioselectivity

Year:  2017        PMID: 27859806     DOI: 10.1002/chem.201604617

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  21 in total

1.  Diastereodivergent Synthesis of Hexahydro-6H-benzo[c]chromen-6-one Derivatives Catalyzed by Modularly Designed Organocatalysts.

Authors:  Satish Jakkampudi; Ramarao Parella; Hadi D Arman; John C-G Zhao
Journal:  Chemistry       Date:  2019-05-09       Impact factor: 5.236

2.  DFT-Based Stereochemical Rationales for the Bifunctional Brønsted Acid/Base-Catalyzed Diastereodivergent and Enantioselective aza-Henry Reactions of α-Nitro Esters.

Authors:  Thomas J Struble; Ivor Smajlagic; Hayden Foy; Travis Dudding; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2021-10-20       Impact factor: 4.354

3.  Ligand-dependent, palladium-catalyzed stereodivergent synthesis of chiral tetrahydroquinolines.

Authors:  Yue Wang; Er-Qing Li; Zheng Duan
Journal:  Chem Sci       Date:  2022-06-20       Impact factor: 9.969

4.  A Diastereodivergent and Enantioselective Approach to syn- and anti-Diamines: Development of 2-Azatrienes for Cu-Catalyzed Reductive Couplings with Imines That Furnish Allylic Amines.

Authors:  Pengfei Zhou; Xinxin Shao; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2021-08-23       Impact factor: 16.383

5.  Complete diastereodivergence in asymmetric 1,6-addition reactions enabled by minimal modification of a chiral catalyst.

Authors:  Daisuke Uraguchi; Ken Yoshioka; Takashi Ooi
Journal:  Nat Commun       Date:  2017-03-20       Impact factor: 14.919

6.  Diastereodivergent asymmetric Michael-alkylation reactions using chiral N,N'-dioxide/metal complexes.

Authors:  Yulong Kuang; Bin Shen; Li Dai; Qian Yao; Xiaohua Liu; Lili Lin; Xiaoming Feng
Journal:  Chem Sci       Date:  2017-11-08       Impact factor: 9.825

7.  Enantioselective synthesis of cyclopenta[b]benzofurans via an organocatalytic intramolecular double cyclization.

Authors:  Bruno Matos Paz; Yang Li; Mathias Kirk Thøgersen; Karl Anker Jørgensen
Journal:  Chem Sci       Date:  2017-10-02       Impact factor: 9.825

8.  Catalyst-Controlled Stereodivergent Synthesis of Atropisomeric Multiaxis Systems.

Authors:  Dominik Lotter; Alessandro Castrogiovanni; Markus Neuburger; Christof Sparr
Journal:  ACS Cent Sci       Date:  2018-05-09       Impact factor: 14.553

9.  Diastereo- and enantioselective additions of α-nitro esters to imines for anti-α,β-diamino acid synthesis with α-alkyl-substitution.

Authors:  Daniel J Sprague; Anand Singh; Jeffrey N Johnston
Journal:  Chem Sci       Date:  2018-01-31       Impact factor: 9.825

10.  Stereodivergent synthesis of vicinal quaternary-quaternary stereocenters and bioactive hyperolactones.

Authors:  Haifeng Zheng; Yan Wang; Chaoran Xu; Xi Xu; Lili Lin; Xiaohua Liu; Xiaoming Feng
Journal:  Nat Commun       Date:  2018-05-17       Impact factor: 14.919

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