Literature DB >> 24734309

Asymmetric Mukaiyama aldol reactions using chiral diamine-coordinated Sn(II) triflate: development and application to natural product synthesis.

Isamu Shiina.   

Abstract

In 1989, the asymmetric Mukaiyama aldol reaction mediated by a Lewis acid consisting of a chiral diamine and Sn(II) triflate was reported. The asymmetric Mukaiyama aldol reaction is now widely used as a versatile tool for the construction of highly advanced, multifunctionalized molecules. In this Personal Account, the history of the development of this powerful methodology and the application of the asymmetric Mukaiyama aldol reaction in the synthesis of natural products are reviewed.

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Year:  2014        PMID: 24734309     DOI: 10.1002/tcr.201300022

Source DB:  PubMed          Journal:  Chem Rec        ISSN: 1528-0691            Impact factor:   6.771


  5 in total

1.  Enantioselective total synthesis of naturally occurring eushearilide and evaluation of its antifungal activity.

Authors:  Takayuki Tonoi; Ryo Kawahara; Takehiko Inohana; Isamu Shiina
Journal:  J Antibiot (Tokyo)       Date:  2016-01-27       Impact factor: 2.649

2.  Total synthesis of the proposed structure of astakolactin.

Authors:  Takayuki Tonoi; Keisuke Mameda; Moe Fujishiro; Yutaka Yoshinaga; Isamu Shiina
Journal:  Beilstein J Org Chem       Date:  2014-10-17       Impact factor: 2.883

3.  Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes.

Authors:  M Emin Cinar; Bernward Engelen; Martin Panthöfer; Hans-Jörg Deiseroth; Jens Schlirf; Michael Schmittel
Journal:  Beilstein J Org Chem       Date:  2016-04-27       Impact factor: 2.883

4.  Chagosensine: A Riddle Wrapped in a Mystery Inside an Enigma.

Authors:  Marc Heinrich; John J Murphy; Marina K Ilg; Aurélien Letort; Jakub T Flasz; Petra Philipps; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2020-03-20       Impact factor: 15.419

5.  Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16Z,20E)-Eushearilide and (16E,20E)-Eushearilide.

Authors:  Takayuki Tonoi; Takehiko Inohana; Teruyuki Sato; Yuuki Noda; Miyuki Ikeda; Miku Akutsu; Takatsugu Murata; Yutaro Maekawa; Anna Tanaka; Rio Seki; Misako Ohkusu; Katsuhiko Kamei; Naruhiko Ishiwada; Isamu Shiina
Journal:  Molecules       Date:  2019-09-22       Impact factor: 4.411

  5 in total

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