Literature DB >> 11428021

A new polymer-anchored chiral catalyst for asymmetric Michael addition reactions.

G Sundararajan1, N Prabagaran.   

Abstract

[figure: see text] Monomer (R,R)-3-aza-3-(p-vinylbenzyl)-1,5-diphenyl-1,5-dihydroxypentane (2) when polymerized with styrene and divinylbenzene affords polymers, onto which lithium and aluminum are incorporated via reaction with lithium aluminum hydride. The resulting insoluble polymers containing chiral lithium and aluminum active centers are quite effective for asymmetric Michael addition of nitro compounds, thiols, and amines. The optimized reaction conditions yield Michael adducts in good yield with high enantiomeric excesses.

Entities:  

Year:  2001        PMID: 11428021     DOI: 10.1021/ol006898e

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

Review 1.  Chalcone: A Privileged Structure in Medicinal Chemistry.

Authors:  Chunlin Zhuang; Wen Zhang; Chunquan Sheng; Wannian Zhang; Chengguo Xing; Zhenyuan Miao
Journal:  Chem Rev       Date:  2017-05-10       Impact factor: 60.622

2.  A Selenourea-Thiourea Brønsted Acid Catalyst Facilitates Asymmetric Conjugate Additions of Amines to α,β-Unsaturated Esters.

Authors:  Yingfu Lin; William J Hirschi; Anuj Kunadia; Anirudra Paul; Ion Ghiviriga; Khalil A Abboud; Rachael W Karugu; Mathew J Vetticatt; Jennifer S Hirschi; Daniel Seidel
Journal:  J Am Chem Soc       Date:  2020-03-11       Impact factor: 15.419

3.  Strain-Release Heteroatom Functionalization: Development, Scope, and Stereospecificity.

Authors:  Justin M Lopchuk; Kasper Fjelbye; Yu Kawamata; Lara R Malins; Chung-Mao Pan; Ryan Gianatassio; Jie Wang; Liher Prieto; James Bradow; Thomas A Brandt; Michael R Collins; Jeff Elleraas; Jason Ewanicki; William Farrell; Olugbeminiyi O Fadeyi; Gary M Gallego; James J Mousseau; Robert Oliver; Neal W Sach; Jason K Smith; Jillian E Spangler; Huichin Zhu; Jinjiang Zhu; Phil S Baran
Journal:  J Am Chem Soc       Date:  2017-02-20       Impact factor: 15.419

4.  Calcium(ii)-catalyzed enantioselective conjugate additions of amines.

Authors:  Brice E Uno; Rachel D Dicken; Louis R Redfern; Charlotte M Stern; Greg G Krzywicki; Karl A Scheidt
Journal:  Chem Sci       Date:  2018-01-10       Impact factor: 9.825

5.  A bifunctional iminophosphorane squaramide catalyzed enantioselective synthesis of hydroquinazolines via intramolecular aza-Michael reaction to α,β-unsaturated esters.

Authors:  Guanglong Su; Connor J Thomson; Ken Yamazaki; Daniel Rozsar; Kirsten E Christensen; Trevor A Hamlin; Darren J Dixon
Journal:  Chem Sci       Date:  2021-03-18       Impact factor: 9.825

6.  Eliminating Transition State Calculations for Faster and More Accurate Reactivity Prediction in Sulfa-Michael Additions Relevant to Human Health and the Environment.

Authors:  Piers A Townsend; Elliot H E Farrar; Matthew N Grayson
Journal:  ACS Omega       Date:  2022-07-21
  6 in total

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