Organocatalytic asymmetric transfer hydrogenation in aqueous media using resin-supported peptide having a polyleucine tether

Organic Letters
Kengo AkagawaKazuaki Kudo

Abstract

A resin-supported N-terminal prolyl peptide having a beta-turn motif and hydrophobic polyleucine chain effectively catalyzed the asymmetric transfer hydrogenation under aqueous conditions. The polyleucine tether provides a hydrophobic cavity in aqueous media that brought about a remarkable acceleration of the reaction. In addition, the polyleucine chain also turned out to be essential for high enantioselectivity.

References

Dec 1, 1999·Bioorganic & Medicinal Chemistry·M J PorterJ Skidmore
Oct 23, 2001·Angewandte Chemie·Peter I. Dalko, Lionel Moisan
Oct 24, 2001·The Journal of Organic Chemistry·Gregory T. CopelandScott J. Miller
Aug 18, 2004·Accounts of Chemical Research·Scott J Miller
Sep 30, 2004·Angewandte Chemie·Peter I Dalko, Lionel Moisan
Jan 6, 2005·Journal of the American Chemical Society·Stéphane G OuelletDavid W C MacMillan
Oct 20, 2005·Biopolymers·Jarred T Blank, Scott J Miller
Oct 27, 2005·Journal of the American Chemical Society·Jung Woon YangBenjamin List
Oct 27, 2005·Journal of the American Chemical Society·Yong HuangDavid W C MacMillan
Jan 5, 2006·Journal of the American Chemical Society·R Ian StorerDavid W C MacMillan
Jan 19, 2006·Journal of the American Chemical Society·Nobuyuki MaseCarlos F Barbas
Feb 24, 2006·Angewandte Chemie·Mark S Taylor, Eric N Jacobsen
May 25, 2006·Angewandte Chemie·Sonja Mayer, Benjamin List
Sep 28, 2006·Journal of the American Chemical Society·Jamison B TuttleDavid W C MacMillan
Oct 5, 2006·Journal of the American Chemical Society·Sebastian HoffmannBenjamin List
Oct 13, 2006·Journal of the American Chemical Society·Nolwenn J A Martin, Benjamin List
Oct 19, 2006·Chemical Communications : Chem Comm·Sanzhong LuoJin-Pei Cheng
May 12, 2007·Angewandte Chemie·Magnus Rueping, Andrey P Antonchick
Jul 3, 2007·Journal of the American Chemical Society·Nolwenn J A MartinBenjamin List

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Citations

Sep 29, 2012·Beilstein Journal of Organic Chemistry·Kengo AkagawaKazuaki Kudo
Nov 20, 2015·Chemical Reviews·Yingfeng TuDaniela A Wilson
Aug 31, 2016·Topics in Current Chemistry·Raquel P Herrera
Dec 29, 2016·Journal of the American Chemical Society·Anthony J MetranoScott J Miller
Feb 24, 2017·Organic & Biomolecular Chemistry·Ana Maria Faísca Phillips, Armando J L Pombeiro
Aug 8, 2015·Chemical Communications : Chem Comm·Amol P JadhavRavi P Singh
Aug 7, 2013·Organic & Biomolecular Chemistry·Xiao-Qing ZhuYuan-Yuan Mu
Apr 29, 2014·Organic & Biomolecular Chemistry·Kengo AkagawaKazuaki Kudo
Feb 1, 2014·Chemistry : a European Journal·Maurizio BernasconiAndreas Pfaltz
Dec 25, 2013·Chemical Society Reviews·Matthieu RaynalPiet W N M van Leeuwen
Jan 28, 2012·Chemical Society Reviews·Chao Zheng, Shu-Li You
Oct 18, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Atsushi UedaMasakazu Tanaka
Jun 9, 2011·Organic Letters·Kengo Akagawa, Kazuaki Kudo
Sep 6, 2017·Accounts of Chemical Research·Kengo Akagawa, Kazuaki Kudo
Jan 14, 2012·Journal of the American Chemical Society·Qing-An ChenYong-Gui Zhou

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