Literature DB >> 33542591

Rational Design of New Dihydrobenzooxophosphole-Based Lewis Base Organocatalysts.

Bo Qu1, Lalith P Samankumara1, Anjan Saha1, Mac G Schumer2, Zhengxu S Han1, Nizar Haddad1, Carl A Busacca1, Nathan K Yee1, Marisa C Kozlowski2, Jinghua J Song1, Chris H Senanayake1.   

Abstract

A series of new dihydrobenzooxophosphole-based Lewis Base organocatalysts were designed and synthesized. They are demonstrated effective in trichlorosilane-mediated stereoselective conjugate reductions of C=C bonds. DFT calculations reveal that the strong hydrogen bond between the amide linker and the chloride on silicon in the transition state contributes to the high reactivity of the catalyst 3a.

Entities:  

Keywords:  Chiral Lewis Base; Enone Reduction; Hydrogen Bonding; Organocatalyst; P(O)NNP(O)

Year:  2020        PMID： 33542591      PMCID： PMC7853668          DOI： 10.1055/s-0039-1690851

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  18 in total

1.  Highly efficient catalyst systems using iron complexes with a tetradentate PNNP ligand for the asymmetric hydrogenation of polar bonds.

Authors:  Christine Sui-Seng; Friederike Freutel; Alan J Lough; Robert H Morris
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Lewis base-catalyzed conjugate reduction and reductive aldol reaction of alpha,beta-unsaturated ketones using trichlorosilane.

Authors:  Masaharu Sugiura; Norimasa Sato; Shunsuke Kotani; Makoto Nakajima
Journal:  Chem Commun (Camb)       Date:  2008-07-17       Impact factor: 6.222

3.  Stereoselective synthesis of multiple stereocenters by using a double aldol reaction.

Authors:  Yasushi Shimoda; Tatsunori Kubo; Masaharu Sugiura; Shunsuke Kotani; Makoto Nakajima
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-18       Impact factor: 15.336

4.  Lewis Base-Catalyzed Enantioselective Conjugate Reduction of β,β-Disubstituted α,β-Unsaturated Ketones with Trichlorosilane: E/Z-Isomerization, Regioselectivity, and Synthetic Applications.

Authors:  Masaharu Sugiura; Yasuhiko Ashikari; Yuka Takahashi; Koki Yamaguchi; Shunsuke Kotani; Makoto Nakajima
Journal:  J Org Chem       Date:  2019-09-09       Impact factor: 4.354

5.  Asymmetric conjugate reduction of alpha,beta-unsaturated ketones and esters with chiral rhodium(2,6-bisoxazolinylphenyl) catalysts.

Authors:  Yoshinori Kanazawa; Yasunori Tsuchiya; Kazuki Kobayashi; Takushi Shiomi; Jun-ichi Itoh; Makoto Kikuchi; Yoshihiko Yamamoto; Hisao Nishiyama
Journal:  Chemistry       Date:  2005-12-16       Impact factor: 5.236

6.  Trichlorosilyl triflate-mediated enantioselective directed cross-aldol reaction between ketones using a chiral phosphine oxide as an organocatalyst.

Authors:  Shohei Aoki; Shunsuke Kotani; Masaharu Sugiura; Makoto Nakajima
Journal:  Chem Commun (Camb)       Date:  2012-04-27       Impact factor: 6.222

7.  Novel, tunable, and efficient chiral bisdihydrobenzooxaphosphole ligands for asymmetric hydrogenation.

Authors:  Wenjun Tang; Bo Qu; Andrew G Capacci; Sonia Rodriguez; Xudong Wei; Nizar Haddad; Bikashandarkoil Narayanan; Shengli Ma; Nelu Grinberg; Nathan K Yee; Dhileep Krishnamurthy; Chris H Senanayake
Journal:  Org Lett       Date:  2010-01-01       Impact factor: 6.005

8.  Efficient asymmetric synthesis of structurally diverse P-stereogenic phosphinamides for catalyst design.

Authors:  Zhengxu S Han; Li Zhang; Yibo Xu; Joshua D Sieber; Maurice A Marsini; Zhibin Li; Jonathan T Reeves; Keith R Fandrick; Nitinchandra D Patel; Jean-Nicolas Desrosiers; Bo Qu; Anji Chen; DiAndra M Rudzinski; Lalith P Samankumara; Shengli Ma; Nelu Grinberg; Frank Roschangar; Nathan K Yee; Guijun Wang; Jinhua J Song; Chris H Senanayake
Journal:  Angew Chem Int Ed Engl       Date:  2015-03-10       Impact factor: 15.336

9.  Atropisomeric chiral dienes in asymmetric catalysis: C(2) -symmetric (Z,Z)-2,3-bis[1-(diphenylphosphinyl)ethylidene]tetralin as a highly active Lewis base organocatalyst.

Authors:  Masamichi Ogasawara; Shunsuke Kotani; Hikaru Nakajima; Haruka Furusho; Mitsuru Miyasaka; Yasushi Shimoda; Wei-Yi Wu; Masaharu Sugiura; Tamotsu Takahashi; Makoto Nakajima
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-25       Impact factor: 15.336

10.  A versatile catalyst system for enantioselective synthesis of 2-substituted 1,4-benzodioxanes.

Authors:  Eugene Chong; Bo Qu; Yongda Zhang; Zachary P Cannone; Joyce C Leung; Sergei Tcyrulnikov; Khoa D Nguyen; Nizar Haddad; Soumik Biswas; Xiaowen Hou; Katarzyna Kaczanowska; Michał Chwalba; Andrzej Tracz; Stefan Czarnocki; Jinhua J Song; Marisa C Kozlowski; Chris H Senanayake
Journal:  Chem Sci       Date:  2019-03-13       Impact factor: 9.825
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