Literature DB >> 15113197

Chirality exchange from sp3 central chirality to axial chirality: benzannulation of optically active diaryl-2,2-dichlorocyclopropylmethanols to axially chiral alpha-arylnaphthalenes.

Yoshinori Nishii1, Kazunori Wakasugi, Keisuke Koga, Yoo Tanabe.   

Abstract

Chirality exchange benzannulation of optically active (1S)-aryl(aryl')-2,2-dichlorocyclopropylmethanols (>99% ee) using TiCl4 successfully proceeded to give axially chiral (M)-alpha-arylnaphthalenes with excellent levels of stereo induction (>99% ee). This unique transformation involves the single-step chirality exchange from sp3 central chirality to axial chirality, that is, a type of excellent memory effect.

Entities:  

Year:  2004        PMID: 15113197     DOI: 10.1021/ja0319442

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  7 in total

1.  Enantioselective synthesis of biphenols from 1,4-diketones by traceless central-to-axial chirality exchange.

Authors:  Fenghai Guo; Leah C Konkol; Regan J Thomson
Journal:  J Am Chem Soc       Date:  2010-12-09       Impact factor: 15.419

2.  Peptide-Catalyzed Fragment Couplings that Form Axially Chiral Non-C2 -Symmetric Biaryls.

Authors:  Gavin Coombs; Marcus H Sak; Scott J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-30       Impact factor: 15.336

3.  A Rhodium(I)-Xylyl-BINAP Catalyzed Asymmetric Ynamide-[2 + 2 + 2] Cycloaddition in the Synthesis of Optically Enriched N,O-Biaryls.

Authors:  Jossian Oppenheimer; Whitney L Johnson; Ruth Figueroa; Ryuji Hayashi; Richard P Hsung
Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

4.  Ipso -Type Regiocontrolled Benzannulation for the Synthesis of Uniquely Substituted α-Arylnaphthalenes: Application to the First Total Synthesis of Chaihunaphthone.

Authors:  Kento Moriguchi; Ryosuke Sasaki; Jun-Ichi Morita; Yoshinobu Kamakura; Daisuke Tanaka; Yoo Tanabe
Journal:  ACS Omega       Date:  2021-07-09

5.  Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes.

Authors:  Changgui Zhao; Donghui Guo; Kristin Munkerup; Kuo-Wei Huang; Fangyi Li; Jian Wang
Journal:  Nat Commun       Date:  2018-02-09       Impact factor: 14.919

6.  Conversion of two stereocenters to one or two chiral axes: atroposelective synthesis of 2,3-diarylbenzoindoles.

Authors:  Yu-Long Hu; Zhe Wang; Hui Yang; Jie Chen; Zi-Bo Wu; Yibo Lei; Ling Zhou
Journal:  Chem Sci       Date:  2019-05-20       Impact factor: 9.825

7.  Synthesis of Naphthaleman Family Utilizing Regiocontrolled Benzannulation: Unique Molecules Composed of Multisubstituted Naphthalenes.

Authors:  Sekiha Ishikawa; Yoshikazu Masuyama; Takeshi Adachi; Takeshi Shimonishi; Shotaro Morimoto; Yoo Tanabe
Journal:  ACS Omega       Date:  2021-11-24
  7 in total

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